HCID 67023507, compound → HCID 67023482, compound

HRID 491890Notes

Reaction equation

HRID 491890 reaction equation
[C:1]([O:5][CH2:6][C@@H:7]([NH:16][C:17](=[O:45])[CH2:18][CH2:19][C@@H:20]([CH:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1)[NH:21][CH2:22][C:23]1[C:28]([N+:29]([O-])=O)=[CH:27][N:26]=[C:25]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:24]=1)[C:8]([N:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:9])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:29][C:28]1[C:23]([CH2:22][NH:21][C@H:20]([CH:39]2[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44]2)[CH2:19][CH2:18][C:17]([NH:16][C@H:7]([CH2:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:8]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[O:9])=[O:45])=[CH:24][C:25]([O:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:26][CH:27]=1

Participants

4

Reactant 1

HCID 67023507HCID 67023507, compound

Product 1

HCID 67023482HCID 67023482, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-(1-(R)-tert-butoxymethyl-2-morpholin-4-yl-2-oxo-ethyl)-4-(S)-cyclohexyl-4-[(5-nitro-2-phenoxy-pyridin-4-ylmethyl)-amino]-butyramide (0.4 g, 0.6 mmol) in MeOH (10 mL) was added 10% Pd on activated carbon (0.1 g) under N2. The reaction mixture was subjected to hydrogenation under 5 psi for 2 h. The catalyst was filtered out, and the MeOH was evaporated to yield 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 as an oil.

Workup

  1. filtrationThe catalyst was filtered out
  2. customthe MeOH was evaporated

Sources & evidence

ORD record
ord-9e94c3cd3e334c1cb47d0db731256077
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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