HCID 66770517, compound → HCID 66771041, compound

HRID 1697634Notes

Reaction equation

HRID 1697634 reaction equation
COC([C@@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C(=S)CC(=O)C)=O.COC([C@H]1C[C@@H](S(C2C=CC=CC=2C(F)(F)F)(=O)=O)CN1C(=S)CC(=O)C)=O.Cl.N(C1C=C(NC(=O)C)C=CC=1)N.[CH3:70][O:71][C:72]([C@H:74]1[CH2:78][C@@H:77]([S:79]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[C:88]([F:91])([F:90])[F:89])(=[O:81])=[O:80])[CH2:76][N:75]1[C:92]1[N:93]([C:98]2[CH:103]=[CH:102][CH:101]=[C:100]([NH:104][C:105](=[O:107])[CH3:106])[CH:99]=2)[N:94]=[C:95]([CH3:97])[CH:96]=1)=[O:73]>>[CH3:70][O:71][C:72]([C@@H:74]1[CH2:78][C@@H:77]([S:79]([C:82]2[CH:87]=[CH:86][CH:85]=[CH:84][C:83]=2[C:88]([F:89])([F:91])[F:90])(=[O:81])=[O:80])[CH2:76][N:75]1[C:92]1[N:93]([C:98]2[CH:103]=[CH:102][CH:101]=[C:100]([NH:104][C:105](=[O:107])[CH3:106])[CH:99]=2)[N:94]=[C:95]([CH3:97])[CH:96]=1)=[O:73]

Participants

5

Reactant 4

HCID 66770517HCID 66770517, compoundHCID 66771276HCID 66771276, compoundHCID 86646823(2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86646844HCID 86646844, compound

Product 1

HCID 66771041HCID 66771041, compound

Procedure

In analogy to the procedure described in example 308d, a mixture of (2S,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester (example 192 g) and of (2R,4R)-1-(3-oxo-thiobutyryl)-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester was reacted with N-(3-hydrazino-phenyl)-acetamide hydrochloride (CAS Reg. No. 1187369-44-3) to give a mixture of the title compound and (2R,4R)-1-[2-(3-acetylamino-phenyl)-5-methyl-2H-pyrazol-3-yl]-4-(2-trifluoromethyl-benzenesulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as yellow solid. MS (ESI): m/z=551.2 [M+H]+.

Workup

  1. custom1187369-44-3) to give

Sources & evidence

ORD record
ord-c38cfb7d49c247f3b5c0e81965f926cb
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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