Acetic Acid → HCID 16727170, compound

HRID 736689Notes

Reaction equation

HRID 736689 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][C:13]3[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([NH2:21])=[O:20])[C:12]=3[N:11]=2)=[CH:6][CH:5]=1)(=O)[CH3:2].[CH:22]1([NH2:26])[CH2:25][CH2:24][CH2:23]1.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH:22]1([NH:26][CH:1]([C:4]2[CH:9]=[CH:8][C:7]([C:10]3[NH:14][C:13]4[CH:15]=[CH:16][CH:17]=[C:18]([C:19]([NH2:21])=[O:20])[C:12]=4[N:11]=3)=[CH:6][CH:5]=2)[CH3:2])[CH2:25][CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 75645CyclobutylamineHCID 5003444Sodium cyanoborohydrideHCID 44542209HCID 44542209, compound

Product 1

HCID 16727170HCID 16727170, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of EXAMPLE 1A (0.07 g, 0.3 mmol) and cyclobutylamine (0.34 mL, 4.8 mmol) in methanol (1 mL) was treated with sodium cyanoborohydride (0.016 g, 0.3 mmol) and acetic acid (0.2 mL). The mixture was stirred at ambient temperature for 48 hours then concentrated. The residue was purified by chromatography on a silica gel column with 0-10% methanol/dichloromethane/0.1% ammonium hydroxide to provide the title compound. 1H NMR (DMSO-d6) δ 9.34 (s, 1H), 8.19 (d, J=7.7 Hz, 2H), 7.86 (d, J=7.7 Hz, 1H), 7.72 (d, J=8.0 Hz, 2H), 7.57 (d, J=7.7 Hz, 2H), 7.34 (t, J=7.7 Hz, 1H), 3.97 (s, 1H), 3.16 (d, J=5.2 Hz, 4H), 2.09 (s, 1H), 1.88 (s, 2H), 1.75 (s, 1H), 1.60 (s, 1H), 1.52 (s, 1H), 1.36 (s, 3H).

Workup

  1. concentrationthen concentrated
  2. customThe residue was purified by chromatography on a silica gel column with 0-10% methanol/dichloromethane/0.1% ammonium hydroxide

Sources & evidence

ORD record
ord-e0400089ff7b406e802d7be0012c191d
Source dataset
uspto-grants-2009_09
Patent number
US07595406B2

Reaction notes

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