tetrahydro-2H-thiopyran-4-ylhydrazine trifluoroacetic acid → (2S,4R)-4-(2-Chlorophenylsulfonyl)-1-(3-methyl-1-(tetrahydro-2H-thiopyran-4-yl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697744Notes

Reaction equation

HRID 1697744 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C@H:11]1[CH2:15][N:14]([C:16](=S)[CH2:17][C:18](=O)[CH3:19])[C@H:13]([C:22]([O:24][CH3:25])=[O:23])[CH2:12]1)(=[O:10])=[O:9].FC(F)(F)C(O)=O.[S:33]1[CH2:38][CH2:37][CH:36]([NH:39][NH2:40])[CH2:35][CH2:34]1>>[CH3:25][O:24][C:22]([C@@H:13]1[CH2:12][C@@H:11]([S:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])(=[O:10])=[O:9])[CH2:15][N:14]1[C:16]1[N:39]([CH:36]2[CH2:37][CH2:38][S:33][CH2:34][CH2:35]2)[N:40]=[C:18]([CH3:19])[CH:17]=1)=[O:23]

Participants

3

Reactant 2

HCID 66771202tetrahydro-2H-thiopyran-4-ylhydrazine trifluoroacetic acidHCID 86646820(2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate

Product 1

HCID 66772245(2S,4R)-4-(2-Chlorophenylsulfonyl)-1-(3-methyl-1-(tetrahydro-2H-thiopyran-4-yl)-1H-pyrazol-5-yl)pyrrolidine-2-carboxylic Acid Methyl Ester

Procedure

In analogy to the procedure described in example 192 h, (2S,4R)-methyl 4-(2-chlorophenylsulfonyl)-1-(3-oxobutanethioyl)pyrrolidine-2-carboxylate (example 253c) was reacted with (tetrahydro-2H-thiopyran-4-yl)hydrazine 2,2,2-trifluoroacetate (CAS Reg. No. 693287-87-5) to give the title compound as yellow foam. MS (ESI): m/z=484.1 [M+H]+.

Sources & evidence

ORD record
ord-48a542409deb4d6c93c2450e7c96b04a
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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