Sodium hydride → HCID 59394139, compound

HRID 1887585Notes

Reaction equation

HRID 1887585 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[C@@H:19]([CH3:20])[CH2:18][C:17]2[C:16]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[NH:27][CH:26]=[CH:25]4)=[N:15][CH:14]=[N:13][C:12]=2[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[C:31]([O:35][C:36]([N:38]1[C:42]([NH:43][C:44](OC2C=CC=CC=2)=[O:45])=[CH:41][C:40]([C:53]2([CH3:56])[CH2:55][CH2:54]2)=[N:39]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[C:3]([O:7][C:8]([N:10]1[C@@H:19]([CH3:20])[CH2:18][C:17]2[C:16]([O:21][C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:44](=[O:45])[NH:43][C:42]3[N:38]([C:36]([O:35][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:37])[N:39]=[C:40]([C:53]5([CH3:56])[CH2:55][CH2:54]5)[CH:41]=3)[CH:26]=[CH:25]4)=[N:15][CH:14]=[N:13][C:12]=2[CH2:11]1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 59394216HCID 59394216, compoundHCID 59394241HCID 59394241, compound

Product 1

HCID 59394139HCID 59394139, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.024 g, 0.990 mmol; 60% in oil) is added to a solution of (S)-4-(1H-Indol-5-yloxy)-6-methyl-5,8-dihydro-6H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester, Example 53-B-1, (0.126 g, 0.330 mmol) and DMF (7.5 mL) at it. After 5 min 3-(1-Methyl-cyclopropyl)-5-phenoxycarbonylamino-pyrazole-1-carboxylic acid tert-butyl ester, Example 5-D, (0.178 g, 0.495 mmol) is then added. After 1 h the mixture is quenched by the addition of saturated aqueous NH4Cl and then concentrated. The residue is separated directly via FCC (20-70% EtOAc/heptane). MS (ESI) m/z 644.2 (M+1).

Workup

  1. customAfter 1 h the mixture is quenched by the addition of saturated aqueous NH4Cl
  2. concentrationconcentrated
  3. customThe residue is separated directly via FCC (20-70% EtOAc/heptane)

Sources & evidence

ORD record
ord-1b882fa7da0345e49a47099a5e58e5ce
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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