HCID 67023458, compound → HCID 178508228, compound

HRID 491883Notes

Reaction equation

HRID 491883 reaction equation
C([O:8][C:9]([CH:11]1[CH2:16][CH2:15][CH:14]([N:17]([C:28](=[O:56])[CH2:29][CH2:30][C@H:31]([N:38]2[CH2:43][C:42]3[CH:44]=[C:45]([O:48][C:49]4[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=4)[N:46]=[CH:47][C:41]=3[N:40]=[C:39]2[NH2:55])[CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:13][CH2:12]1)=[O:10])C1C=CC=CC=1>CCO.[Pd]>[NH2:55][C:39]1[N:38]([C@H:31]([CH:32]2[CH2:37][CH2:36][O:35][CH2:34][CH2:33]2)[CH2:30][CH2:29][C:28]([N:17]([CH2:18][CH2:19][O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C@@H:14]2[CH2:13][CH2:12][C@H:11]([C:9]([OH:10])=[O:8])[CH2:16][CH2:15]2)=[O:56])[CH2:43][C:42]2[CH:44]=[C:45]([O:48][C:49]3[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=3)[N:46]=[CH:47][C:41]=2[N:40]=1

Participants

4

Reactant 1

HCID 67023458HCID 67023458, compound

Product 1

HCID 178508228HCID 178508228, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-[[4-(2-Amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cyclohexanecarboxylic acid benzyl ester (0.4 g, 0.42 mmol) and Pd (10% on carbon, 0.2 g) in EtOH (50 mL) was subjected to hydrogenation under 10 psi for 48 h. HPLC purification yielded 4-[[4-(2-Amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S-(tetrahydro-pyran-4-yl)-butyryl]-(2-hydroxy-ethyl)-amino]-cyclohexanecarboxylic acid as a white solid and 4-[[4-(2-Amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid as a white solid.

Workup

  1. customHPLC purification

Sources & evidence

ORD record
ord-2a81bc7d91fe4dd590201218ce5a6e08
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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