Hydrochloric Acid → HCID 178466831, compound

HRID 872866Notes

Reaction equation

HRID 872866 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH3:31])[CH2:15][N:16]2[CH:20]=[C:19]([Cl:21])[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=3)=[N:17]2)=[O:12])[NH:8][N:7]=1)(=[O:5])[CH3:4].Cl>C(O)C.O>[Cl:21][C:19]1[C:18]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=2)=[N:17][N:16]([CH2:15][C@@H:14]([NH:13][C:11]([C:9]2[NH:8][N:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:10]=2)=[O:12])[CH3:31])[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 70656475(S)-3-acetyl-N-(1-(4-chloro-3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 178466831HCID 178466831, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 0° C. solution containing sodium tetrahydroborate (0.022 g, 0.580 mmol) dissolved in ethanol (1 ml), (S)-3-acetyl-N-(1-(4-chloro-3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide (0.125 g, 0.290 mmol) of Example 224 dissolved in 2 ml of ethanol was added slowly. The mixture was stirred at 0° C. for a few minutes after which the mixture was allowed to warm to RT and the stirring was continued for 4.5 h. A few drops of water was added slowly. The pH was adjusted below 4 with 2 M HCl. The solvent was evaporated and the residue extracted with DCM/water. Organic phase was isolated with phase separator and evaporated. The product was purified by recrystallization from ethanol. Yield 51.0%. 1H-NMR (400 MHz; DMSO-d6): δ 1.14 (d, 3H), 1.38 (d, 3H), 4.23-4.37 (m, 2H), 4.40-4.50 (m, 1H), 4.75-4.83 (m, 1H), 5.40 (d, 1H), 6.40 (s, 1H), 8.00 (dd, 1H), 8.04 (dd, 1H), 8.05-8.14 (m, 3H), 13.03 (s, 1H).

Workup

  1. additionwas added slowly
  2. temperatureto warm to RT
  3. customThe solvent was evaporated
  4. extractionthe residue extracted with DCM/water
  5. customOrganic phase was isolated with phase separator
  6. customevaporated
  7. customThe product was purified by recrystallization from ethanol

Sources & evidence

ORD record
ord-550f256ac7ec44f68206541f7b9d2122
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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