Diisopropylethylamine → HCID 178433048, 화합물

HRID 872797노트

반응식

HRID 872797 반응식
[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]

참가 물질

8

반응물 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, 화합물

생성물 1

HCID 178433048HCID 178433048, 화합물수율 71.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f8f663e9b5d14e53a00ccad4b3c8d697
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08975254B2

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