Acetic Acid → HCID 135939594, compound

HRID 1927277Notes

Reaction equation

HRID 1927277 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:21]=[C:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1.O=[CH:23][CH2:24][NH:25]C(=O)OC(C)(C)C.C([BH3-])#N.[Na+].C(O)(=O)C>C(O)C.C(#N)C>[NH2:25][CH2:24][CH2:23][NH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:21]=[C:11]3[NH:12][C:13](=[O:20])[C:14]4[C:19]([N:10]3[N:9]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5003444Sodium cyanoborohydrideHCID 135939592HCID 135939592, compound

Product 1

HCID 135939594HCID 135939594, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

A solution of EXAMPLE 12 (0.06 g, 0.2 mmol) and tert-butyl (2-oxoethyl)carbamate (0.035 g, 0.2 mmol) in ethanol (1 mL) and acetonitrile (1 mL) was treated with sodium cyanoborohydride (0.014 g, 0.2 mmol) and acetic acid (0.2 mL). The mixture was heated in a microwave at 170° C. for 40 minutes and concentrated. The residue was purified by flash chromatography on silica gel with 10% methanol/dichloromethane/0.1% ammonium hydroxide to provide the title compound. 1H NMR (DMSO-d6) δ 12.30 (s, 1H), 10.06 (s, 1H), 8.11-8.19 (m, 2H), 7.89-7.96 (m, 1H), 7.58-7.67 (m, 2H), 7.52 (t, J=7.6 Hz, 1H), 7.39 (t, J=7.9 Hz, 1H), 6.27 (s, 1H), 3.30-3.36 (m, 4H), 2.08 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography on silica gel with 10% methanol/dichloromethane/0.1% ammonium hydroxide

Sources & evidence

ORD record
ord-23c913fe4e90475cb2a63bedc99e362d
Source dataset
uspto-grants-2012_05
Patent number
US08183250B2

Reaction notes

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