Acetic Acid → HCID 136242908, compound

HRID 1775201Notes

Reaction equation

HRID 1775201 reaction equation
O=[C:2]1[C:14]2[C:13]3[C:12]([C:15]([O:17]C)=O)=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH2:5][N:4]([C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:3]1.C(O)(=O)C.O.[NH2:34][NH2:35]>CO>[O:17]=[C:15]1[C:12]2=[CH:11][CH:10]=[CH:9][C:8]3[NH:7][C:6]4[CH2:5][N:4]([C:19]([O:21][CH2:22][C:23]5[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=5)=[O:20])[CH2:3][C:2]([C:14]=4[C:13]=32)=[N:35][NH:34]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 89657570HCID 89657570, compound

Product 1

HCID 136242908HCID 136242908, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of compound 2-benzyl 5-methyl 4-oxo-3,4-dihydro-1H-pyrido[3,4-b]indole-2,5(9H)-dicarboxylate (70 mg, 0.18 mmol), acetic acid (0.15 mL, 2.6 mmol), and hydrazine hydrate (0.86 mL, 1.5 mmol) in methanol (4 mL) was heated at reflux. After 8 h, the solid was collected by hot filtration and washed with water, EtOAc, and dichloromethane, to give the target compound (61 mg, 94%). 1H NMR DMSO-d6) δ 11.8 (s, 1H), 10.1 (s, 1H), 7.54 (d, 1H, J=8.4 Hz), 7.48 (d, 1H, J=7.2 Hz), 7.38 (m, 4H), 7.32 (m, 1H), 7.18 (dd, 1H, J=8.4, 7.2 Hz), 5.15 (s, 2H), 4.82 (m, 2H), 4.28 (m, 2H). MS (ESI) m/e [M+1]+ 361.

Workup

  1. temperatureat reflux
  2. filtrationthe solid was collected by hot filtration
  3. washwashed with water, EtOAc, and dichloromethane

Sources & evidence

ORD record
ord-7ff256c02f0d425bb19efdf37762b198
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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