(2S,5R)-1-[(tert-butoxy)carbonyl]-5-phenylpyrrolidine-2-carboxylic acid → (2S,5R)-tert-Butyl 2-((2-(6-(2-acetamidobenzo[d]thiazol-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)-5-phenylpyrrolidine-1-carboxylate

HRID 1594484Notes

Reaction equation

HRID 1594484 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:11][CH2:10][C@H:9]1[C:19](O)=[O:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:22][C:23]1[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][C:24]=1[C:33]1[N:38]=[CH:37][N:36]=[C:35]([O:39][C:40]2[C:45]3[N:46]=[C:47]([NH:49][C:50](=[O:52])[CH3:51])[S:48][C:44]=3[CH:43]=[CH:42][CH:41]=2)[CH:34]=1>>[C:50]([NH:49][C:47]1[S:48][C:44]2[CH:43]=[CH:42][CH:41]=[C:40]([O:39][C:35]3[N:36]=[CH:37][N:38]=[C:33]([C:24]4[CH:25]=[CH:26][C:27]([C:29]([F:32])([F:30])[F:31])=[CH:28][C:23]=4[NH:22][C:19]([C@@H:9]4[CH2:10][CH2:11][C@H:12]([C:13]5[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=5)[N:8]4[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:20])[CH:34]=3)[C:45]=2[N:46]=1)(=[O:52])[CH3:51]

Participants

3

Reactant 2

HCID 2755972(2S,5R)-1-[(tert-butoxy)carbonyl]-5-phenylpyrrolidine-2-carboxylic acidHCID 21865046N-(4-(6-(2-Amino-4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 58691342(2S,5R)-tert-Butyl 2-((2-(6-(2-acetamidobenzo[d]thiazol-4-yloxy)pyrimidin-4-yl)-5-(trifluoromethyl)phenyl)carbamoyl)-5-phenylpyrrolidine-1-carboxylate

Procedure

(2S,5R)-1-(tert-Butoxycarbonyl)-5-phenylpyrrolidine-2-carboxylic acid (350 mg, 1.2 mmol, Neosystem-T) was reacted with N-(4-(6-(2-amino-4-(trifluoromethyl)-phenyl)pyrimidin-4-yloxy)benzo[d]thiazol-2-yl)acetamide (446 mg, 1.0 mmol, prepared as described in WO04014871) under the conditions of Example 45(a) to give the title compound as a white solid. MS (ESI, neg. ion.) m/z: 719 (M−1).

Sources & evidence

ORD record
ord-34caca6864664b61a9d37aea3b8ba8d2
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

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