Acetic Acid → HCID 44610986, compound

HRID 2387560Notes

Reaction equation

HRID 2387560 reaction equation
F[C:2]1[CH:3]=[C:4]([S:12]([N:15]([CH3:29])[C@@H:16]2[CH2:24][CH2:23][CH2:22][C:21]3[N:20]([CH2:25][C:26]([OH:28])=[O:27])[N:19]=[CH:18][C:17]2=3)(=[O:14])=[O:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[NH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(O)(=O)C>CS(C)=O>[CH3:29][N:15]([S:12]([C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=[C:2]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)[CH:3]=1)(=[O:13])=[O:14])[C@@H:16]1[CH2:24][CH2:23][CH2:22][C:21]2[N:20]([CH2:25][C:26]([OH:28])=[O:27])[N:19]=[CH:18][C:17]1=2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 59152933HCID 59152933, compound

Product 1

HCID 44610986HCID 44610986, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
180 °C

Procedure

{(R)-4-[(3-Fluoro-5-trifluoromethyl-benzenesulfonyl)-methyl-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid (25 mg, 0.066 mmol) and pyrrolidine (47 mg, 0.66 mmol) were dissolved in dimethyl sulfoxide (1.5 mL). The mixture was heated in a microwave oven at 180° C. for 50 minutes. The resulting mixture was acidified with acetic acid to pH 4, and then filtered and purified by preparative HPLC to afford {(R)-4-[methyl-(3-pyrrolidin-1-yl-5-trifluoromethyl-benzenesulfonyl)-amino]-4,5,6,7-tetrahydro-indazol-1-yl}-acetic acid (15 mg, 48.5%) as a white powder. 1H NMR (400 MHz, CD3OD) δ ppm 7.24 (s, 1H), 7.14 (s, 1H), 6.98 (s, 1H), 6.41 (s, 1 H), 5.05 (t, 1H), 4.75 (s, 2H), 3.35 (t, 4H), 2.61 (s, 3H), 2.45 (m, 2H), 2.08-1.61 (m, 8H). MS calcd. for C21H25F3N4O4S 486, obsd. (ESI+) [(M+H)+] 487.

Workup

  1. filtrationfiltered
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c1bfcb0b8c3e44dda953a82705b99048
Source dataset
uspto-grants-2012_09
Patent number
US08268870B2

Reaction notes

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