Ammonium Chloride → HCID 178422087, compound

HRID 872561Notes

Reaction equation

HRID 872561 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][C@@H:12]([CH3:29])[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])[C:20]=3[CH3:28])=[N:15]2)=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+].[Cl-].[NH4+]>C(O)C>[Cl:27][C:21]1[C:20]([CH3:28])=[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])[CH3:29])[N:15]=2)[CH:24]=[CH:23][C:22]=1[C:25]#[N:26]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 70655829(S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-propan-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 178422087HCID 178422087, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-3-acetyl-N-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)-propan-2-yl)-1H-pyrazole-5-carboxamide (0.04 g, 0.097 mmol) as prepared in the previous Example was added in ethanol (5 ml). Solid sodium borohydride (0.018 g, 0.487 mmol) was added to the mixture and it was refluxed for 15 min under nitrogen. To the cooled solution a portion of 10 ml of saturated ammonium chloride was added and the mixture was extracted several times with DCM. The organic extracts were combined and washed with water, dried with Na2SO4, filtered and evaporated to dryness affording 0.040 g of the title compound. 1H-NMR (400 MHz; CDCl3): δ 1.25 (m, 3H), 1.51 (m, 3H), 2.49 (d, 3H), 3.72 (m, 1H), 4.29 (m, 1H), 4.41 (m, 1H), 4.61 (m, 1H), 4.99 (m, 1H), 6.42 (d, 1H), 6.56 (s, 1H), 7.43-7.50 (m, 3H), 7.53 (d, 1H).

Workup

  1. temperaturewas refluxed for 15 min under nitrogen
  2. extractionthe mixture was extracted several times with DCM
  3. washwashed with water
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-0bcb73d9d5354aeca575e030504e3161
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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