Methylamine → tert-butyl ((5-(2-fluorophenyl)-1-((3-(2-(methylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

HRID 1051004Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]([CH2:10][C:11]1[CH:12]=[C:13]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=2[F:37])[N:14]([S:16]([C:19]2[CH:20]=[C:21]([CH:28]=[CH:29][CH:30]=2)[O:22][CH2:23][C:24]([O:26]C)=O)(=[O:18])=[O:17])[CH:15]=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:38][NH2:39]>CO>[F:37][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=1[C:13]1[N:14]([S:16]([C:19]2[CH:30]=[CH:29][CH:28]=[C:21]([O:22][CH2:23][C:24]([NH:39][CH3:38])=[O:26])[CH:20]=2)(=[O:17])=[O:18])[CH:15]=[C:11]([CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH:12]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 2-(3-((4-(((tert-butoxycarbonyl)(methyl)amino)methyl)-2-(2-fluorophenyl)-1H-pyrrol-1-yl)sulfonyl)phenoxy)acetate 1i (110 mg, 0.20 mmol) was dissolved in 10 mL of a solution of methylamine in methanol (33%), and the reaction solution was heated up to 40° C. and stirred for 2 h. The reaction solution was concentrated under reduced pressure to obtain the title product tert-butyl ((5-(2-fluorophenyl)-1-((3-(2-(methylamino)-2-oxoethoxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 1j (60 mg, a yellow oil), which was used directly in the next step.

Workup

concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-33a5d5c86c9c479d9f3113ab7915e39f
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388133B2

Reaction notes

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