Methanesulfonyl chloride → [4-Amino-2-(1-methanesulfonylpiperidin-4-ylamino)thiazol-5-yl]-(3-fluoro-4-methoxy-phenyl)methanone
Reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([NH:18][CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1)=[O:8].[CH3:25][S:26](Cl)(=[O:28])=[O:27]>>[NH2:1][C:2]1[N:3]=[C:4]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([S:26]([CH3:25])(=[O:28])=[O:27])[CH2:21][CH2:20]2)[S:5][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1)=[O:8]Participants
3
Procedure
[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluoro4-methoxy-phenyl)methanone (0.11 g, 0.31 mmol) (Example 7) was treated with methanesulfonyl chloride in a manner similar to Example 9 to give 30 mg (23% yield) of [4-amino-2-(1-methanesulfonylpiperidin-4-ylamino)thiazol-5-yl]-(3-fluoro-4-methoxy-phenyl)methanone. 1H NMR (DMSO−d6, 300 MHz) δ1.46 (m, 2H, CH2), 2.01 (m, 2H, CH2), 2.90 (m, 5H, CH2 & SCH3), 3.55(m, 2HCH2), 3.6-4.0 (broad, 1H, CH), 3.91 (s, 3H, OCH3), 7.24 (t,1H, Aromatic), 7.47 (t,1H, Aromatic), 7.59 (t,1H, Aromatic), 7.9-8.5 (brd, 2H, 2NH), 8.71 (brd, 1H, NH). HRMSEI: (M+H)+: observed: 428.0982; calcd for 428.0988.
Sources & evidence
- ORD record
- ord-a58c7159c4f14b3fb5c8a6aaa1d1020c
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07423053B2
Reaction notes
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