(2S)-2-(trifluoromethyl)pyrrolidine → (S)-3-[(4-(2-(Trifluoromethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

HRID 587151Notes

Reaction equation

HRID 587151 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1.[F:20][C:21]([F:28])([F:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][NH:23]1>>[F:20][C:21]([F:28])([F:27])[C@@H:22]1[CH2:26][CH2:25][CH2:24][N:23]1[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:10]=[C:11]([CH2:15][S:16]([NH2:19])(=[O:18])=[O:17])[CH:12]=[CH:13][CH:14]=2)[N:3]=1

Participants

3

Reactant 2

HCID 2782840(2S)-2-(trifluoromethyl)pyrrolidineHCID 866798223-[(4-Chloro-1,3,5-triazin-2-yl)amino]benzenemethanesulfonamide

Product 1

HCID 60197303(S)-3-[(4-(2-(Trifluoromethyl)pyrrolidin-1-yl)-1,3,5-triazin-2-yl)amino]-benzenemethanesulfonamide

Procedure

B16 was prepared following the general procedure reported for B10 using A1 and (S)-2-(trifluoromethyl)pyrrolidine. The title compound (B16) was purified by reverse phase RP-HPLC (column: C18), using H2O (0.1% TFA) and MeOH (0.1% TFA) as eluents. Yield: 58.7 mg (15%), colorless amorphous solid. MS (ES) C15H17F3N6O2S requires: 402. found: 403 (M+H)+.

Workup

  1. customB16 was prepared
  2. customThe title compound (B16) was purified by reverse phase RP-HPLC (column: C18)

Sources & evidence

ORD record
ord-74e0f034a70b4ffe8cda917fb76a7e99
Source dataset
uspto-grants-2016_01
Patent number
US09226929B2

Reaction notes

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