Potassium Carbonate → HCID 68972864, compound

HRID 1726282Notes

Reaction equation

HRID 1726282 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:30][C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)[CH:9]2[CH2:14][CH2:13][N:12]([C@H:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19]([C:21]3[C:22]([CH3:28])=[N:23][CH:24]=[N:25][C:26]=3[CH3:27])=[O:20])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Br[CH2:37][C:38]([O:40][CH3:41])=[O:39].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:41][O:40][C:38](=[O:39])[CH2:37][O:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C@H:15]([CH3:29])[CH2:16][CH2:17][NH:18][C:19]([C:21]3[C:26]([CH3:27])=[N:25][CH:24]=[N:23][C:22]=3[CH3:28])=[O:20])[CH2:13][CH2:14]2)[CH2:30][C:31]2[CH:35]=[CH:34][S:33][CH:32]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57563184HCID 57563184, compound

Product 1

HCID 68972864HCID 68972864, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of COMPOUND 296 (290 mg, 0.59 mmol), methyl bromoacetate (141 mg, 0.92 mmol) and K2CO3 (123 mg, 0.89 mmol) in DMF (5.8 mL) was heated at 80° C. overnight to afford {4-[(1-{(R)-3-[(4,6-dimethyl-pyrimidine-5-carbonyl)-amino]-1-methyl-propyl}-piperidin-4-yl)-thiophen-3-ylmethyl-amino]-phenoxy}-acetic acid methyl ester as a brown oil (145 mg, 42%) following work-up and purification.

Sources & evidence

ORD record
ord-20ab3b5ced2047f1a336be60a16d1284
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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