Hydrochloric Acid → HCID 178466823, compound

HRID 872510Notes

Reaction equation

HRID 872510 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][C@@H:12]([CH3:28])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([Cl:27])[CH:20]=3)=[N:15]2)=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].CCO.[BH4-].[Na+].Cl>O>[Cl:27][C:21]1[CH:20]=[C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH2:13][C@@H:12]([NH:11][C:9]([C:7]3[NH:6][N:5]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:8]=3)=[O:10])[CH3:28])[N:15]=2)[CH:24]=[CH:23][C:22]=1[C:25]#[N:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 4311764Sodium borohydrideHCID 52919826(S)-5-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-3-carboxamide

Product 1

HCID 178466823HCID 178466823, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(S)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide (100 mg; 0.25 mmol) and 5 ml of EtOH were put to reaction flask and sodium borohydride (19 mg; 0.5 mmol) was added slowly as EtOH suspension. The reaction was stirred overnight to completion. 0.5 ml of water and 1 ml of 0.5M HCl were added dropwise. The solution was evaporated to dryness, 20 ml of DCM was added and washed with 10 ml of 1 M NaHCO3 and 10 ml of water followed with drying over Na2SO4. After filtration and evaporation 76 mg (76%) of pure title compound was obtained. 1H-NMR (400 MHz; d6-DMSO): δ 1.11 (d, 3H), 1.38 (d, 3H), 4.22-4.48 (m, 3H), 4.74-4.84 (m, 1H), 4.41 (d, 1H), 6.40 (s, 1H), 6.94 (d, 1H), 7.81 (d, 1H), 7.92-8.05 (m, 2H), 8.09 (d, 1H), 8.20 (d, 1H), 13.04 (s, 1H).

Workup

  1. customThe solution was evaporated to dryness, 20 ml of DCM
  2. additionwas added
  3. washwashed with 10 ml of 1 M NaHCO3 and 10 ml of water
  4. dry with materialwith drying over Na2SO4
  5. filtrationAfter filtration
  6. customevaporation 76 mg (76%) of pure title compound
  7. customwas obtained

Sources & evidence

ORD record
ord-57da619ded7547e4b1b9fba5434aa46f
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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