Methyl 2-bromopropionate → HCID 58315412, compound

HRID 2359582Notes

Reaction equation

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

Participants

Reactant 2

HCID 95576Methyl 2-bromopropionate

HCID 44631912Ribociclib

Product 1

HCID 58315412HCID 58315412, compoundYield 39%

Procedure

Following General Procedure D, 7-cyclopentyl-2-(5-piperazin-1-yl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (100 mg, 0.230 mmol) and 2-bromo propionic acid methyl ester (31 mL, 0.28 mmol) gave 2-{4-[6-(7-cyclopentyl-6-dimethylcarbamoyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)-pyridin-3-yl]-piperazin-1-yl}-propionic acid methyl ester (46 mg, 39%). MS (ESI) m/z 521.4 (M+H)+

Sources & evidence

ORD record: ord-b42c265852294f4e86cb68cf3f5d90a0
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685980B2

Reaction notes

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