Sodium borohydride → HCID 73855059, compound

HRID 1242026Notes

Reaction equation

HRID 1242026 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:34][CH2:35][CH3:36])=[C:8]([N:10]=[C:11]2[N:15]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:14](=[O:23])[C:13](=[C:24]3[N:28]([CH3:29])[C:27]4[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=4[S:25]3)[S:12]2)[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C1COCC1>[CH2:16]([N:15]1[C:14](=[O:23])[C:13](=[C:24]2[N:28]([CH3:29])[C:27]3[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=3[S:25]2)[S:12][C:11]1=[N:10][C:8]1[CH:9]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:5]=[CH:6][C:7]=1[NH:34][CH2:35][CH3:36])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 73855027HCID 73855027, compound

Product 1

HCID 73855059HCID 73855059, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The product of Example 38 was reduced with sodium borohydride in 1:1 MeOH/THF and chromatographed (TEA-washed silica gel, 0–10% MeOH/DCM) to afford the title compound. 1H-NMR (CDCl3): δ 7.47–7.54 (3H, m), 7.28–7.37 (4H, m), 7.17 (1H, m), 6.99–7.06 (3H, m), 6.57 (1H, d), 5.19 (2H, s), 4.80 (1H, q), 3.76 (3H, s), 3.01 (2H, q), 1.48 (3H, d), 1.04 (3H, s); MS(ESI): 517 (MH+).

Workup

  1. customchromatographed
  2. wash(TEA-washed silica gel, 0–10% MeOH/DCM)

Sources & evidence

ORD record
ord-9f8e4b0239444ea7b98beaa0f81f0d17
Source dataset
uspto-grants-2006_10
Patent number
US07115640B2

Reaction notes

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