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Methanesulfonyl chloride → 4-[4-Fluoro-2-((S)-1-methanesulfonyl-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

HRID 240614
Notes
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Reaction equation

HRID 240614 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:28][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][C@H:22]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)[C:7]=2[C:6]=1[CH3:29])=[O:4].CCN(C(C)C)C(C)C.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>ClCCl>[CH3:1][O:2][C:3]([C:5]1[S:28][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[O:21][C@H:22]3[CH2:27][CH2:26][CH2:25][N:24]([S:40]([CH3:39])(=[O:42])=[O:41])[CH2:23]3)[C:7]=2[C:6]=1[CH3:29])=[O:4]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 58413182HCID 58413182, compound

Product 1

HCID 584131414-[4-Fluoro-2-((S)-1-methanesulfonyl-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Procedure

To a solution of 4-[4-fluoro-2-((S)-piperidin-3-yloxy)-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (110 mg) in dichloromethane (3 ml) at 0° C. was added DIPEA (55 μl) followed by methanesulfonyl chloride (25 μl) and the reaction was allowed to warm to room temperature and stirred for 2 h.

Sources & evidence

ORD record
ord-6921ebe0be384fd298b9e5fc279eb56a
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08648068B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes