Trifluoroacetic acid → tert-Butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)benzyl(methyl)carbamate

HRID 75439Notes

Reaction equation

HRID 75439 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[N:12]=[C:11]([C:20]3[CH:25]=[CH:24][C:23]([NH:26][C:27](=[O:45])[NH:28][C:29]4[CH:44]=[CH:43][C:32]([CH2:33][N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[CH:31][CH:30]=4)=[CH:22][CH:21]=3)[N:10]=1)[CH2:2]2.FC(F)(F)C(O)=O>ClCCl>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([CH2:15][S:16]([CH3:19])(=[O:17])=[O:18])[N:12]=[C:11]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:27](=[O:45])[NH:28][C:29]4[CH:30]=[CH:31][C:32]([CH2:33][N:34]([CH3:42])[C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:40])[CH3:38])=[CH:43][CH:44]=4)=[CH:24][CH:25]=3)[N:10]=1)[CH2:2]2.[CH:5]12[O:8][CH:1]([CH2:7][CH2:6]1)[CH2:2][N:3]([C:9]1[CH:14]=[C:13]([CH2:15][S:16]([CH3:19])(=[O:17])=[O:18])[N:12]=[C:11]([C:20]3[CH:21]=[CH:22][C:23]([NH:26][C:27]([NH:28][C:29]4[CH:30]=[CH:31][C:32]([CH2:33][NH:34][CH3:35])=[CH:43][CH:44]=4)=[O:45])=[CH:24][CH:25]=3)[N:10]=1)[CH2:4]2

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 49764258tert-Butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)benzyl(methyl)carbamate

Product 2

HCID 49764258tert-Butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)benzyl(methyl)carbamateHCID 49764512HCID 49764512, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)benzyl(methyl)carbamate was prepared as described above. Removal of the Boc group in tert-butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(methylsulfonylmethyl)pyrimidin-2-yl)phenyl)ureido)benzyl(methyl)carbamate (98.3 mgs, 0.154 mmoles) by treatment with trifluoroacetic acid in dichloromethane gave the title compound. Yield: 70.8 mg (86%). RT 1.63, M+H=537.2.

Sources & evidence

ORD record
ord-f0747616e7324ce1bfd5b787f3f97613
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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