Oxalyl chloride → 1,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carbonyl chloride

HRID 1785950Notes

Reaction equation

HRID 1785950 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]([C:24]3C=NN(C(C)C)[CH:28]=3)=[O:23])[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C(N1C=C(C([Cl:43])=O)C=N1)(C)C.[CH3:44][N:45]1[C:49]2[S:50][C:51]([C:53](O)=[O:54])=[CH:52][C:48]=2[C:47]([CH3:56])=[N:46]1.C(Cl)(=O)C(Cl)=O>ClCCl.CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22]([C:24]3[S:50][C:49]4[N:45]([CH3:44])[N:46]=[C:47]([CH3:56])[C:48]=4[CH:28]=3)=[O:23])[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:6][CH:7]=1.[CH3:44][N:45]1[C:49]2[S:50][C:51]([C:53]([Cl:43])=[O:54])=[CH:52][C:48]=2[C:47]([CH3:56])=[N:46]1

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 27765411,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acidHCID 11510715HCID 11510715, compoundHCID 60136483HCID 60136483, compound

Product 2

HCID 27765421,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carbonyl chlorideHCID 11648888HCID 11648888, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-(4-Chlorophenyl)-N-{(2S,4R)-1-[(1,3-dimethyl-1H-thieno[2,3-c]pyrazol-5-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide was prepared following the procedure for N-(4-chlorophenyl)-N-{(2S,4R)-1-[(1-isopropyl-1H-pyrazol-4-yl)carbonyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}acetamide substituting 1,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carbonyl chloride for 1-isopropyl-1H-pyrazole-4-carbonyl chloride. (1,3-Dimethyl-1H-thieno[2,3-c]pyrazole-5-carbonyl chloride was prepared from commercially available 1,3-dimethyl-1H-thieno[2,3-c]pyrazole-5-carboxylic acid by treatment with oxalyl chloride and catalytic DMF in dichloromethane).

Sources & evidence

ORD record
ord-a92fb496713c4fc5871cfb210e11746e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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