Hydrochloric Acid → HCID 24802774, compound

HRID 2094222Notes

Reaction equation

HRID 2094222 reaction equation
C([O:3][C:4](=O)[CH2:5][CH:6]([N:8]1[CH:12]=[N:11][N:10]=[C:9]1[C:13]1[C:18]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([C:30]([F:33])([F:32])[F:31])[CH:24]=2)(=[O:22])=[O:21])=[CH:17][C:16]([Cl:34])=[CH:15][N:14]=1)[CH3:7])C.[BH4-].[Li+].C1COCC1.Cl>CO>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([NH:19][C:18]2[C:13]([C:9]3[N:8]([CH:6]([CH3:7])[CH2:5][CH2:4][OH:3])[CH:12]=[N:11][N:10]=3)=[N:14][CH:15]=[C:16]([Cl:34])[CH:17]=2)(=[O:21])=[O:22])=[CH:24][C:25]=1[C:30]([F:32])([F:31])[F:33]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 59216831HCID 59216831, compound

Product 1

HCID 24802774HCID 24802774, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-{3-[5-Chloro-3-(4-chloro-3-trifluoromethyl-benzenesulfonylamino)-pyridin-2-yl]-[1,2,4]triazol-4-yl}-butyric acid ethyl ester (27 mg, 0.05 mmol), lithium borohydride (2.0M, 0.14 ml, 0.28 mmol), 1.5 ml of THF and 0.02 ml of methanol was stirred at room temperature for 2 hours. The mixture was mixed with diluted HCl (1.0M), extracted with ethyl acetate, and the extracts were combined and washed with brine and dried. After concentration the residue was purified by prep TLC to afford title compound as a white solid. 1H NMR: (DMSO-d6, ppm): 9.03 (s, 1H), 8.30 (m, 1H), 8.11 (m, 1H), 8.02 (m, 1H), 7.91 (m, 1H), 7.83 (m, 1H), 3.28 (m, 1H), 3.19 (m, 2H), 1.91 (m, 2H), 1.42 (d, 3H). MS (ES) [M+H]+ expected 510.0. found 510.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. customdried
  4. concentrationAfter concentration the residue
  5. customwas purified by prep TLC

Sources & evidence

ORD record
ord-cb85476bcca9470ea41d256f4069a309
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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