Sodium borohydride → HCID 178456031, compound

HRID 872583Notes

Reaction equation

HRID 872583 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:10]=[C:9]([C:11]([NH:13][C@@H:14]([CH2:30][CH3:31])[CH2:15][N:16]2[CH:20]=[CH:19][C:18]([C:21]3[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[C:23]([Cl:29])[CH:22]=3)=[N:17]2)=[O:12])[NH:8][N:7]=1)(=[O:5])[CH3:4]>CCO>[Cl:29][C:23]1[CH:22]=[C:21]([C:18]2[CH:19]=[CH:20][N:16]([CH2:15][C@@H:14]([NH:13][C:11]([C:9]3[NH:8][N:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:10]=3)=[O:12])[CH2:30][CH3:31])[N:17]=2)[CH:26]=[CH:25][C:24]=1[C:27]#[N:28]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67173060HCID 67173060, compound

Product 1

HCID 178456031HCID 178456031, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a cooled (0° C.) solution of sodium borohydride (12 mg, 0.32 mmol) in 2 ml of dry EtOH was added (S)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)butan-2-yl)-1H-pyrazole-5-carboxamide of Example 99 (66 mg, 0.16 mmol) as a solution in 3 ml of dry EtOH. Reaction mixture was stirred at RT overnight before being quenched by adding some water and 0.5 M HCl until pH was acidic. Solvents were evaporated and the evaporation residual was taken up in 5% MeOH in DCM, washed with 1 M NaHCO3 solution and water. Organic phase was dried over Na2SO4, filtered and evaporated to yield 64 mg (96%) of the title compound. 1H-NMR (400 MHz; CDCl3/MeOD): δ 1.00 (t, 3H), 1.48-1.65 (m, 5H), 4.29-4.43 (m, 3H), 4.94 (q, 1H), 6.59-6.62 (m, 2H), 7.52 (d, 1H), 7.67-7.72 (m, 1H), 7.78-7.82 (m, 1H), 7.99-8.01 (m, 1H).

Workup

  1. customReaction mixture
  2. custombefore being quenched
  3. additionby adding some water and 0.5 M HCl until pH
  4. customSolvents were evaporated
  5. washwashed with 1 M NaHCO3 solution and water
  6. dry with materialOrganic phase was dried over Na2SO4
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-65bc47da19664e6c803a1cb3a699af7a
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

Loading…