Cyanogen Bromide → HCID 57678340, compound

HRID 491891Notes

Reaction equation

HRID 491891 reaction equation
[NH2:1][C:2]1[C:3]([CH2:15][NH:16][C@H:17]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)[CH2:18][CH2:19][C:20]([NH:22][C@H:23]([CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])=[O:21])=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1.Br[C:45]#[N:46]>CCO>[NH2:46][C:45]1[N:16]([C@H:17]([CH:38]2[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]2)[CH2:18][CH2:19][C:20]([NH:22][C@H:23]([CH2:32][O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[C:24]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[O:25])=[O:21])[CH2:15][C:3]2[CH:4]=[C:5]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[N:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 67023482HCID 67023482, compound

Product 1

HCID 57678340HCID 57678340, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-[(5-amino-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-(1-(R)-tert-butoxymethyl-2-morpholin-4-yl-2-oxo-ethyl)-4-(S)-cyclohexyl-butyramide (0.37 g, 0.6 mmol) and BrCN (3M in CH2Cl2, 0.25 mL) in EtOH (20 mL) was stirred at room temperature overnight. The EtOH was evaporated to yield an oil, which was purified by Gilson HPLC to yield 4-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-N-(1-(R)-tert-butoxymethyl-2-morpholin-4-yl-2-oxo-ethyl)-4-(S)-cyclohexyl-butyramide as a white solid, as its corresponding TFA salt.

Workup

  1. customThe EtOH was evaporated
  2. customto yield an oil, which
  3. customwas purified by Gilson HPLC

Sources & evidence

ORD record
ord-0a52000b14ab4f038d765028c00f7259
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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