Methyl bromoacetate → HCID 67538379, compound

HRID 45140Notes

Reaction equation

HRID 45140 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[F:7][C:8]([F:40])([F:39])[C:9]1[CH:10]=[C:11]([NH:15][C:16]([N:18]2[C:26]3[C:21](=[CH:22][C:23]([O:27][C:28]4[C:29]5[CH2:37][CH:36]([CH3:38])[NH:35][CH2:34][C:30]=5[N:31]=[CH:32][N:33]=4)=[CH:24][CH:25]=3)[CH:20]=[CH:19]2)=[O:17])[CH:12]=[CH:13][CH:14]=1>C(#N)C>[CH3:6][O:5][C:3](=[O:4])[CH2:2][N:35]1[CH:36]([CH3:38])[CH2:37][C:29]2[C:28]([O:27][C:23]3[CH:22]=[C:21]4[C:26](=[CH:25][CH:24]=3)[N:18]([C:16](=[O:17])[NH:15][C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([C:8]([F:7])([F:39])[F:40])[CH:10]=3)[CH:19]=[CH:20]4)=[N:33][CH:32]=[N:31][C:30]=2[CH2:34]1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 59394590HCID 59394590, compound

Product 1

HCID 67538379HCID 67538379, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl bromoacetate (0.15 mL, 1.58 mmol) is added to a solution of 5-(6-methyl-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethyl-phenyl)-amide, Example 52-B, (0.370 g, 0.792 mmol) and TEA (0.44 mL, 3.17 mmol) in ACN (10 mL). The solution is allowed to stir overnight. The solution is then concentrated and the residue separated directly via FCC (30-100% EtOAc/heptane) to give {6-methyl-4-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-5,8-dihydro-6H-pyrido[3,4-d]pyrimidin-7-yl}-acetic acid methyl ester.

Workup

  1. concentrationThe solution is then concentrated
  2. customthe residue separated directly via FCC (30-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-693066dae4f74b9cb01b1b27b5716653
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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