4-Fluorobenzoic Acid → N-[7-(dimethylcarbamoylmethyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

HRID 51873Notes

Reaction equation

HRID 51873 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([NH:13][CH3:14])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:22][C:23]([N:25]([CH3:27])[CH3:26])=[O:24].[F:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][CH:30]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C>CN(C=O)C.C1COCC1>[CH3:26][N:25]([CH3:27])[C:23]([CH2:22][N:13]([CH3:14])[C:6]1[C:7]2[S:11][C:10]([NH:12][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][C:29]([F:28])=[CH:30][CH:31]=3)=[N:9][C:8]=2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:24]

Participants

9

Reactant 6

HCID 99734-Fluorobenzoic AcidHCID 11430Potassium CarbonateHCID 520502-Iodo-N,N-dimethylacetamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 227369784-methoxy-N7-methyl-benzothiazole-2,7-diamine

Product 1

HCID 10173236N-[7-(dimethylcarbamoylmethyl-methyl-amino)-4-methoxy-benzothiazol-2-yl]-4-fluoro-benzamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

From 4-methoxy-N7-methyl-benzothiazole-2,7-diamine with potassium carbonate and 2-iodo-N,N-dimethyl-acetamide in DMF, then treatment with 4-fluorobenzoic acid, HATU and N-ethyldiisopropylamine in THF. ES-MS m/e (%): 417 (M+H+, 100).

Sources & evidence

ORD record
ord-5f2c6b2f66ea485b89c80b899f9af508
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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