Sodium borohydride → HCID 59009442, compound

HRID 737211Notes

Reaction equation

HRID 737211 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16](=[O:31])[NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23]2[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=2)[N:22]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86616449HCID 86616449, compound

Product 1

HCID 59009442HCID 59009442, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-[4-(4-Cyano-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (100 mg, 0.23 mmol) was suspended in 10 mL of dry EtOH. To this suspension was added NaBH4 (12.8 mg, 0.46 mmol) followed by CoCl2 (60 mg, 0.46 mmol). Reaction mixture was stirred at room temperature for 4 hours. Reaction mixture was filtered and filtrate concentrated under reduced pressure to yield crude product which was then purified using reverse phase HPLC. MS: 433.1 (M+H+); H1 NMR (MeOH-d4): δ(ppm) 8.00 (d, 2H), 7.49 (m, 3H), 7.37 (m, 2H), 7.18 (d, 1H), 7.02 (m, 2H), 5.03 (m, 2H), 4.49 (m, 1H), 4.16 (s, 2H), 3.96 (m, 2H), 3.61 (m, 2H), 2.39 (m, 1H), 1.99 (m, 4H).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationwas filtered
  4. concentrationfiltrate concentrated under reduced pressure
  5. customto yield crude product which
  6. customwas then purified

Sources & evidence

ORD record
ord-ab87bfa4536b4deaa60941e3fbfca458
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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