Cyanogen Bromide → HCID 178508229, compound

HRID 491882Notes

Reaction equation

HRID 491882 reaction equation
[CH2:1]([O:8][C:9]([C@H:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([C:28](=[O:54])[CH2:29][CH2:30][C@H:31]([NH:38][CH2:39][C:40]2[C:45]([NH2:46])=[CH:44][N:43]=[C:42]([O:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)[CH:41]=2)[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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:56]#[N:57]>CCO>[CH2:1]([O:8][C:9]([C@H:11]1[CH2:12][CH2:13][C@@H:14]([N:17]([C:28](=[O:54])[CH2:29][CH2:30][C@H:31]([N:38]2[CH2:39][C:40]3[CH:41]=[C:42]([O:47][C:48]4[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=4)[N:43]=[CH:44][C:45]=3[N:46]=[C:56]2[NH2:57])[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)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178508038HCID 178508038, compound

Product 1

HCID 178508229HCID 178508229, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[[4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-4-(S)-(tetrahydro-pyran-4-yl)-butyryl]-(2-benzyloxy-ethyl)-amino]-cis-cyclohexanecarboxylic acid benzyl ester (0.5 g, 0.7 mmol) and BrCN (3M in CH2Cl2, 0.25 mL) in EtOH (20 mL) was stirred at room temperature overnight. The EtOH was evaporated. The resulting oil was stirred in diethyl ether (50 mL) for 30 min. 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 benzyl ester was collected as a solid as its corresponding HBr salt.

Workup

  1. customThe EtOH was evaporated
  2. custom4-[[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 benzyl ester was collected as a solid as its corresponding HBr salt

Sources & evidence

ORD record
ord-974faa967ce545c1aefa186647926335
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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