Diisopropylethylamine → HCID 178433048、化合物

HRID 872797ノート

反応式

HRID 872797 の反応式
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([C:7]([OH:9])=O)[N:6]=1.CN(C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.CN(C)CCCN=C=NCC.CCN(C(C)C)C(C)C.[NH2:55][C@@H:56]([CH3:72])[CH2:57][N:58]1[CH:62]=[CH:61][C:60]([C:63]2[CH:70]=[CH:69][C:66]([C:67]#[N:68])=[C:65]([Cl:71])[CH:64]=2)=[N:59]1>CN(C)C=O.O>[Cl:71][C:65]1[CH:64]=[C:63]([C:60]2[CH:61]=[CH:62][N:58]([CH2:57][C@@H:56]([NH:55][C:7]([C:5]3[N:6]=[C:2]([CH3:1])[NH:3][CH:4]=3)=[O:9])[CH3:72])[N:59]=2)[CH:70]=[CH:69][C:66]=1[C:67]#[N:68]

参加物

8

反応物 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67170882(S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrileHCID 178433052HCID 178433052、化合物

生成物 1

HCID 178433048HCID 178433048、化合物収率 71.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-Methyl-1H-imidazole-4-carboxylic acid (1.364 g, 10.82 mmol) was suspended in N,N-Dimethyl formamide (25 ml). 0-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluroniumhexafluorophosphate (0.342 g, 0.901 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.073 g, 10.82 mmol), DIPEA (3.14 ml, 18.03 mmol) and (S)-4-(1-(2-aminopropyl)-1H-pyrazol-3-yl)-2-chlorobenzonitrile (2.5 g, 9.01 mmol) were rapidly added into the mixture, respectively. The reaction mixture was stirred at RT overnight. Next day water was slowly added and the mixture was extracted twice with DCM. The combined organic phases were extracted three times with water and the DCM-layer was evaporated. The product was crystallized from acetonitrile/water mixture and finally dried with vacuum at 40° C. Yield 71.6%. 1H-NMR (400 MHz; d6-DMSO): δ 1.08 (d, 3H), 2.31 (s, 3H), 4.27 (dd, 1H), 4.32-4.48 (m, 2H), 6.95 (d, 1H), 7.41 (s, 1H), 7.82 (d, 1H), 7.95-8.02 (m, 2H), 8.04 (d, 1H), 8.10 (m, 1H), 12.10 (bs, 1H).

後処理

  1. extractionthe mixture was extracted twice with DCM
  2. extractionThe combined organic phases were extracted three times with water
  3. customthe DCM-layer was evaporated
  4. customThe product was crystallized from acetonitrile/water mixture
  5. customfinally dried with vacuum at 40° C

出典と根拠

ORDレコード
ord-f8f663e9b5d14e53a00ccad4b3c8d697
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

反応ノート

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