Sodium borohydride → HCID 71557439, compound

HRID 1411685Notes

Reaction equation

HRID 1411685 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:13][C:12]2[CH:11]=[C:10]3[N:5]([CH2:6][CH2:7][N:8]([C:15]4[C:20]([CH:21]=[O:22])=[C:19]([C:23]5[CH:28]=[C:27]([NH:29][C:30]6[CH:35]=[C:34]([CH3:36])[N:33]=[C:32]([CH3:37])[N:31]=6)[C:26](=[O:38])[N:25]([CH3:39])[CH:24]=5)[CH:18]=[CH:17][N:16]=4)[C:9]3=[O:14])[C:4]=2[CH2:3]1.[BH4-].[Na+]>CO>[CH3:37][C:32]1[N:31]=[C:30]([NH:29][C:27]2[C:26](=[O:38])[N:25]([CH3:39])[CH:24]=[C:23]([C:19]3[CH:18]=[CH:17][N:16]=[C:15]([N:8]4[CH2:7][CH2:6][N:5]5[C:4]6[CH2:3][C:2]([CH3:40])([CH3:1])[CH2:13][C:12]=6[CH:11]=[C:10]5[C:9]4=[O:14])[C:20]=3[CH2:21][OH:22])[CH:28]=2)[CH:35]=[C:34]([CH3:36])[N:33]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86684309HCID 86684309, compound

Product 1

HCID 71557439HCID 71557439, compoundYield 17.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

At 0° C., to a solution of 173c (290 mg, 0.54 mmol) in methanol (5 mL) was added sodium borohydride (62 mg, 1.62 mmol). The reaction mixture was stirred at room temperature for 20 minutes and quenched with water (1 mL). It was then concentrated under reduced pressure and the residue was purified by reverse-phase prep-HPLC to afford 173 as white solid (50 mg, 17%). MS-ESI: [M+H]+ 540.3. 1H NMR (500 MHz, CDCl3) δ 8.90 (d, J=2.5 Hz, 1H), 8.51 (d, J=5.0 Hz, 1H), 8.01 (d, J=2.0 Hz, 1H), 8.00 (s, 1H), 7.35 (d, J=5.5 Hz, 1H), 6.85 (s, 1H), 6.45 (s, 1H), 5.16-5.13 (m, 1H), 4.67-4.52 (m, 2H), 4.33-4.29 (m, 1H), 4.16 (d, J=5.0 Hz, 2H), 3.90-3.86 (m, 1H), 3.72 (s, 3H), 2.58-2.56 (m, overlap, 5H), 2.51 (s, 2H), 2.40 (s, 3H), 2.02 (s, 6H).

Workup

  1. customquenched with water (1 mL)
  2. concentrationIt was then concentrated under reduced pressure
  3. customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-e670e74a371a4b87b5d04318f70bc051
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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