Sodium borohydride → HCID 70655807, compound

HRID 872647Notes

Reaction equation

HRID 872647 reaction equation
[BH4-].[Na+].C([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([C:13](=[O:32])[NH:14][C@H:15]([CH3:31])[CH2:16][N:17]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=3)=[N:18]2)[N:12]=1)=O)C>C(O)C>[Cl:30][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][N:17]([CH2:16][C@H:15]([NH:14][C:13]([C:11]3[N:12]=[C:8]([CH2:6][OH:5])[S:9][CH:10]=3)=[O:32])[CH3:31])[N:18]=2)[CH:27]=[CH:26][C:25]=1[C:28]#[N:29]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67172332HCID 67172332, compound

Product 1

HCID 70655807HCID 70655807, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (108 mg, 2.85 mmol) was added into a flask and the atmosphere was replaced with nitrogen. Dry ethanol was added and the reaction mixture was cooled to 0° C. (R)-ethyl-4-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)thiazole-2-carboxylate (632.8 mg, 1.426 mmol) was added and the reaction mixture was warmed slowly to RT while stirring overnight. The crude product was cooled to 0° C., the pH was adjusted to 6 and the mixture was evaporated. DCM and a few drops of ethanol were added and the crude product was washed with 1M Na2CO3 and with water. The final product was triturated using diethyl ether and DCM with some heptane added dropwise. Yield 46.6%. 1H-NMR (400 MHz; DMSO-d6): δ 1.12 (d, 3H), 4.31 (dd, 1H), 4.40 (dd, 1H), 4.43-4.51 (m, 1H), 4.78 (s, 2H), 6.20 (s, 1H), 6.95 (d, 1H), 7.84 (d, 1H), 7.95 (dd, 1H), 7.98 (dd, 1H), 8.08 (dd, 1H), 8.13 (s, 1H), 8.50 (d, 1H).

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. additionDCM and a few drops of ethanol were added
  4. washthe crude product was washed with 1M Na2CO3 and with water
  5. customThe final product was triturated
  6. additionadded dropwise

Sources & evidence

ORD record
ord-0c7224c951f3462ca32b25914a5bf302
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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