N-carbobenzyloxyalanine → (S)-((R)-1-(4-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl-carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-(benzyloxy-carbonylamino)propanoate

HRID 1517886Notes

Reaction equation

HRID 1517886 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[C:26](=[O:41])[N:27]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:28]([CH2:31][C@H:32]([OH:34])[CH3:33])[C:29]=2[CH3:30])=[O:24])=[CH:18][C:17]=1[F:42].[C:43]([NH:53][C@H:54]([C:56](O)=[O:57])[CH3:55])([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[C:26](=[O:41])[N:27]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[N:28]([CH2:31][C@H:32]([O:34][C:56](=[O:57])[C@@H:54]([NH:53][C:43]([O:45][CH2:46][C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:44])[CH3:55])[CH3:33])[C:29]=2[CH3:30])=[O:24])=[CH:18][C:17]=1[F:42]

Participants

3

Reactant 2

HCID 736104N-carbobenzyloxyalanineHCID 59598358(R)-N-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide

Product 1

HCID 86645606(S)-((R)-1-(4-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl-carbamoyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydropyrazol-1-yl)propan-2-yl)2-(benzyloxy-carbonylamino)propanoate

Procedure

The title compound was prepared according to the procedure described in Example of 73 Step 6 by using (R)—N-(4-(6,7-dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-1-(2-hydroxypropyl)-5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazole-4-carboxamide (4.1 g, 7.2 mmol), (S)—N-Cbz-alanine (3.2 g, 14.4 mmol). The title compound was obtained as a white powder (4.2 g, 75.1%).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6cd276c38097457686960f28b8034691
Source dataset
uspto-grants-2012_07
Patent number
US08232294B2

Reaction notes

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