Cyanogen Bromide → HCID 178508227, compound

HRID 491887Notes

Reaction equation

HRID 491887 reaction equation
[CH:1]1([C@@H:7]([NH:25][CH2:26][C:27]2[C:32]([N+:33]([O-])=O)=[CH:31][N:30]=[C:29]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[CH:28]=2)[CH2:8][CH2:9][C:10]([N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[O:11])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N:43]#[C:44]Br>C(O)C.C1COCC1.[Pd]>[NH2:43][C:44]1[N:25]([C@H:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9][C:10]([N:12]([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:13][C:14]2[NH:18][N:17]=[N:16][N:15]=2)=[O:11])[CH2:26][C:27]2[CH:28]=[C:29]([O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[N:30]=[CH:31][C:32]=2[N:33]=1

Participants

6

Reactant 2

HCID 10476Cyanogen BromideHCID 178520643HCID 178520643, compound

Product 1

HCID 178508227HCID 178508227, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(S),N-dicyclohexy-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-N-(1H-tetrazol-5-ylmethyl)-butyramide (0.75 g, 1.3 mmole) in ethanol (30 mL) and THF (20 mL) was added palladium on carbon (10%, 0.48 g). The reaction mixture was hydrogenated for 1 hour at 20 psi. The reaction mixture was then filtered. Cyanogen bromide (3 M in dichloromethane, 0.65 ml, 1.9 mmole) was added, and the reaction mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the resulting residue was purified by reverse phase HPLC to yield 4-{[4-(2-amino-6-phenoxy-4H-pyrido[3,4-d]pyrimidin-3-yl)-4-(S),N-dicyclohexyl-N-(1H-tetrazol-5-ylmethyl)-butyramide as a white solid, as its corresponding TFA salt.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationThe reaction mixture was concentrated
  3. customthe resulting residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-1311391e5d24403390079c27e515f47f
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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