Potassium Carbonate → HCID 57961824, compound

HRID 541952Notes

Reaction equation

CS(O[CH2:6][CH2:7][S:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH:15][C:16]2[C:21]([Cl:22])=[CH:20][N:19]=[C:18]([Cl:23])[N:17]=2)[CH:10]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH2:30][C:31]1[CH:32]=[C:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=[CH:35][CH:36]=1>CN(C)C=O>[Cl:23][C:18]1[N:17]=[C:16]([NH:15][C:11]2[CH:10]=[C:9]([S:8][CH2:7][CH2:6][NH:30][C:31]3[CH:32]=[C:33]([NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])[CH:34]=[CH:35][CH:36]=3)[CH:14]=[CH:13][CH:12]=2)[C:21]([Cl:22])=[CH:20][N:19]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A solution of 2-({3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}thio)ethyl methanesulfonate (0.17 g, 0.43 mmol) in N,N-dimethylformamide (2 mL) was treated with potassium carbonate (0.15 g, 1.1 mmol) followed by tert-butyl (3-aminophenyl)carbamate (0.17 g, 0.81 mmol) and stirred at 20° C. for 16 h. The reaction mixture was purified by preparative LCMS to give the desired product (23 mg, 10% for 2 steps). LCMS for C23H26Cl2N5O2S (M+H)+: m/z=505.9, 508.0.

Workup

customThe reaction mixture was purified by preparative LCMS

Sources & evidence

ORD record: ord-ef8ce27df05147a2aea01fc39e0c4c66
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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