Acetyl chloride → 1-[4-[4-Amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone

HRID 30157Notes

Reaction equation

HRID 30157 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].[C:25](Cl)(=[O:27])[CH3:26]>>[NH2:1][C:2]1[N:3]=[C:4]([NH:18][CH:19]2[CH2:24][CH2:23][N:22]([C:25](=[O:27])[CH3:26])[CH2:21][CH2:20]2)[S:5][C:6]=1[C:7](=[O:8])[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([F:17])[CH:10]=1

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 11951612[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone

Product 1

HCID 119516181-[4-[4-Amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanoneYield 77%

Procedure

[4-Amino-2-(piperidin-4-ylamino)thiazol-5-yl]-(3-fluoro4-methoxy-phenyl)methanone (0.125 g, 0.36 mmol) (Example 7) was treated with acetylchloride in a manner similar to Example 9 to give 100 mg (77% yield) of 1-[4-[4-amino-5-(3-fluoro-4-methoxybenzoyl)thiazol-2-ylamino]piperidin-1-yl]ethanone. 1H NMR (DMSO−d6, 300 MHz) δ1.38 (dm, 2H, CH2), 1.92 (m, 2H, CH2), 2.02 (s, 3H, COCH3), 2.76 (t, 1H, NCH), 3.26 (t, 1H, NCH), 3.6-4.0 (broad, 1H, CH), 3.77 (m, 1H, NCH), 3.90 (s, 3H, OCH3), 4.22 (m, 1H, NCH), 7.23 (t, 1H, Aromatic), 7.47 (t, 1H, Aromatic), 7.50 (t, 1H, Aromatic), 7.9-8.5 (brd, 2H, 2NH), 8.69 (brd, 1H, NH). HRMS: (M+H)+: observed: 393.1396; calcd for 393.1391.

Sources & evidence

ORD record
ord-21982bed22ba4e78b9953d628c953907
Source dataset
uspto-grants-2008_09
Patent number
US07423053B2

Reaction notes

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