Sodium borohydride → HCID 70656343, compound

HRID 872677Notes

Reaction equation

HRID 872677 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([CH3:33])=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([C:28](OCC)=[O:29])[S:26][CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11]>C(O)C>[Cl:3][C:4]1[C:5]([CH3:33])=[C:6]([C:12]2[CH:16]=[CH:15][N:14]([CH2:17][C@@H:18]([NH:20][C:21]([C:23]3[N:24]=[C:25]([CH2:28][OH:29])[S:26][CH:27]=3)=[O:22])[CH3:19])[N:13]=2)[CH:7]=[CH:8][C:9]=1[C:10]#[N:11]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86670255HCID 86670255, compound

Product 1

HCID 70656343HCID 70656343, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (14.21 mg, 0.376 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. (S)-ethyl 4-(1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamoyl)thiazole-2-carboxylate (86 mg, 0.188 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 7 and the mixture was evaporated. DCM and a few drops of methanol were added and the crude product was washed with 1M Na2CO3 and with water. Yield 89%. 1H-NMR (400 MHz; DMSO-d6): δ 1.13 (d, 3H), 2.53 (s, 3H), 4.23 (dd, 1H), 4.40 (dd, 1H), 4.49 (m, 1H), 4.75 (d, 2H), 6.21 (t, 1H), 6.62 (d, 1H), 7.64 (dd, 1H), 7.82 (dd, 1H), 7.85 (d, 1H), 8.13 (s, 1H), 8.43 (d, 1H).

Workup

  1. additionwas added
  2. customthe mixture was evaporated
  3. additionDCM and a few drops of methanol were added
  4. washthe crude product was washed with 1M Na2CO3 and with water

Sources & evidence

ORD record
ord-308073cd02384afeb3960ccf9d0ce326
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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