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Triethylamine → 4-Methyl-piperazine-1-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide

HRID 1928719
ノート
印刷プレビュー

反応式

HRID 1928719 の反応式
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:21])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.ClC(Cl)(O[C:33](=[O:39])OC(Cl)(Cl)Cl)Cl.[CH3:41][N:42]1[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]1>O1CCCC1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:21][C:33]([N:45]4[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]4)=[O:39])[CH:17]=3)[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]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

6

反応物 4

HCID 8471Triethylamine2 回HCID 531671-MethylpiperazineHCID 94429TriphosgeneHCID 57860958(R)-N2-Indan-1-yl-quinoline-2,6-diamine

生成物 1

HCID 442174734-Methyl-piperazine-1-carboxylic acid [2-((R)-indan-1-ylamino)-quinolin-6-yl]-amide収率 118.3%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
80 °C

実験手順

(R)—N2-Indan-1-yl-quinoline-2,6-diamine (0.25 g, 0.9 mmol) was dissolved in tetrahydrofuran (10 mL) and triethylamine (0.138 mL, 1.0 mmol) was added. At 0° C. triphosgene (121 mg, 0.4 mmol) was added and the reaction mixture subsequently heated to 80° C. for 3 h. Upon cooling to ambient temperature triethylamine (0.138 mL, 1.0 mmol) and 1-methyl-piperazine (0.1 mL, 0.9 mmol) were added and the whole reaction mixture was stirred over night at 50° C. After evaporation of the solvent, the residue was taken up in water and extracted with ethyl acetate. The combined organic phases were dried on sodium sulfate, filtered and the filtrate was evaporated. The residue was taken up in a small amount of ethyl acetate, sonicated and kept over night in a refrigerator whereby a crystalline precipitate formed. The precipitate was isolated and dried on vacuum to yield the title compound (190 mg; 52%) as an off-white solid; MS: m/e=402.6 (M+H+).

後処理

  1. additionwere added
  2. customthe whole reaction mixture
  3. customAfter evaporation of the solvent
  4. extractionextracted with ethyl acetate
  5. customThe combined organic phases were dried on sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated
  8. customsonicated
  9. waitkept over night in a refrigerator whereby
  10. customa crystalline precipitate formed
  11. customThe precipitate was isolated
  12. customdried on vacuum

出典と根拠

ORDレコード
ord-23f348de158e452a97caf0523d661d98
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08183380B2

反応ノート

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