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4-Methylmorpholine → (2-{2-(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(R)-cyclohexyl-ethyl)-carbamic acid methyl ester

HRID 636998
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HRID 636998 반응식
[CH3:1][O:2][C:3]([NH:5][C@H:6]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14]([OH:16])=O)=[O:8])=[O:4].[NH2:23][CH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([NH2:35])=[N:30][CH:29]=[CH:28]2.CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:4])[NH:5][C@H:6]([CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:7]([N:9]1[CH2:13][CH2:12][CH2:11][C@H:10]1[C:14](=[O:16])[NH:23][CH2:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[C:31]([NH2:35])=[N:30][CH:29]=[CH:28]2)=[O:8]
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참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 221697756-(Aminomethyl)isoquinolin-1-amineHCID 229584911-[(R)-methoxycarbonylamino-cyciohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid

생성물 1

HCID 53684487(2-{2-(S)-[(1-Amino-isoquinolin-6-ylmethyl)-carbamoyl]-pyrrolidin-1-yl}-2-oxo-1-(R)-cyclohexyl-ethyl)-carbamic acid methyl ester
수율 58%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1-[(R)-methoxycarbonylamino-cyclohexyl-acetyl]-pyrrolidine-2-(S)-carboxylic acid (0.410 g), 6-aminomethyl-isoquinolin-1-ylamine (0.227 g), N-methyl morpholine (0.58 mL) and 0.423 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) in 10 mL of dry N,N-dimethyl formamide was stirred for 3 h at ambient temperature. The mixture was concentrated and the remaining residue was purified by BPLC (RP-18; H2OCH3OH 95/5→0/100) to give 0.350 g (58%) of the title compound as a white solid. (+)-APCI-MS: 468 (MH+).

후처리

  1. concentrationThe mixture was concentrated
  2. customthe remaining residue was purified by BPLC (RP-18; H2OCH3OH 95/5→0/100)

출처 및 근거

ORD 기록
ord-a185d0c5b2814d1fb47351afcad0f979
출처 데이터셋
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06194409B1

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