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1-Hydroxybenzotriazole → HCID 21984036、化合物

HRID 9496
ノート
印刷プレビュー

反応式

HRID 9496 の反応式
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][O:5][CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:7]1[CH:15]=[CH:14][C:10]([C:11](O)=[O:12])=[CH:9][CH:8]=1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[NH2:45][CH2:46][CH2:47][CH2:48][CH2:49][N:50]1[C:62]2[C:61]3[CH:60]=[CH:59][C:58]([C:63]4[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=4)=[CH:57][C:56]=3[N:55]=[C:54]([NH2:69])[C:53]=2[N:52]=[C:51]1[CH2:70][O:71][CH2:72][CH3:73]>C(Cl)(Cl)Cl.CC(N(C)C)=O>[NH2:69][C:54]1[C:53]2[N:52]=[C:51]([CH2:70][O:71][CH2:72][CH3:73])[N:50]([CH2:49][CH2:48][CH2:47][CH2:46][NH:45][C:11](=[O:12])[C:10]3[CH:9]=[CH:8][C:7]([CH:6]([O:5][CH2:4][CH2:3][N:2]([CH3:22])[CH3:1])[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[CH:15][CH:14]=3)[C:62]=2[C:61]2[CH:60]=[CH:59][C:58]([C:63]3[CH:64]=[N:65][CH:66]=[CH:67][CH:68]=3)=[CH:57][C:56]=2[N:55]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15453776HCID 15453776、化合物HCID 672820741-(4-aminobutyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-4-amine

生成物 1

HCID 21984036HCID 21984036、化合物収率 61.9%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 31374Dimethylacetamide溶媒

反応条件

温度
0 °C

実験手順

A mixture of 4-[(2-dimethylaminoethoxy)phenylmethyl]benzoic acid (0.433 g) and 1-hydroxybenzotriazole (0.196 g) in chloroform (7 mL) was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.277 g) was added in small portions over a 2 minute period. The mixture was stirred for 1 hour and then added dropwise to a chilled (0° C.) solution of 1-(4-aminobutyl)-2-ethoxymethyl-7-(pyridin-3-yl)-1 H-imidazo[4,5-c]quinolin-4-amine (0.400 g) in anhydrous dimethylacetamide (7 mL). The cooling bath was removed and the reaction was stirred for an additional 16 hours. Water was added and the mixture was made acidic by the addition of 4N hydrochloric acid. The aqueous fraction was extracted with diethyl ether (3×) to remove the dimethylacetamide. Sodium hydroxide (10% in water) was added to make the aqueous fraction basic and the aqueous fraction was subsequently extracted with multiple portions of dichloromethane. The organic fractions were combined, washed sequentially with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography using a gradient of CMA/chloroform as the eluent. A final recrystallization from acetonitrile provided 0.426 g of N-[4-(4-amino-2-ethoxymethyl-7-(pyridin-3-yl)imidazo[4,5-c]quinolin-1-yl)butyl]-4-[(2-dimethylaminoethoxy)phenylmethyl]benzamide as a white crystalline solid, mp 157.0–161.0° C.

後処理

  1. additionadded dropwise to
  2. customThe cooling bath was removed
  3. stirringthe reaction was stirred for an additional 16 hours
  4. additionWater was added
  5. additionthe mixture was made acidic by the addition of 4N hydrochloric acid
  6. extractionThe aqueous fraction was extracted with diethyl ether (3×)
  7. customto remove the dimethylacetamide
  8. additionSodium hydroxide (10% in water) was added
  9. extractionthe aqueous fraction was subsequently extracted with multiple portions of dichloromethane
  10. washwashed sequentially with water and brine
  11. dry with materialdried over sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe residue was purified by flash column chromatography
  15. customA final recrystallization from acetonitrile

出典と根拠

ORDレコード
ord-e6aae422c5174d3cb16088d3a37e9cb7
出典データセット
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07091214B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート