Acetyl chloride → N-[7-(acetyl-benzyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

HRID 51881Notes

Reaction equation

HRID 51881 reaction equation
[CH2:1]([NH:8][C:9]1[C:17]2[S:16][C:15]([NH2:18])=[N:14][C:13]=2[C:12]([O:19][CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](Cl)(=[O:23])[CH3:22].[F:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>ClCCl.C1COCC1.N1C=CC=CC=1>[C:21]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[C:17]2[S:16][C:15]([NH:18][C:30](=[O:31])[C:29]3[CH:33]=[CH:34][C:26]([F:25])=[CH:27][CH:28]=3)=[N:14][C:13]=2[C:12]([O:19][CH3:20])=[CH:11][CH:10]=1)(=[O:23])[CH3:22]

Participants

9

Reactant 5

HCID 6367Acetyl chlorideHCID 79724-MethylmorpholineHCID 99734-Fluorobenzoic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22737000N7-benzyl-4-methoxy-benzothiazole-2,7-diamine

Product 1

HCID 10127509N-[7-(acetyl-benzyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

From N7-benzyl-4-methoxy-benzothiazole-2,7-diamine with pyridine and acetyl chloride in dichloromethane and THF, then treatment with 4-fluorobenzoic acid, HATU and N-methylmopholine in THF. ES-MS m/e (%): 450 (M+H+, 100).

Sources & evidence

ORD record
ord-fdbe74ff741d41f59f5e7a62d7ca17fe
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

Loading…