Dichloromethane → HCID 178435360, compound

HRID 1587511Notes

Reaction equation

HRID 1587511 reaction equation
[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([NH2:55])=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[N:29]=[N:30][N:31](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:32]=2)=[CH:18][CH:17]=1)[CH3:2].[Cl:56]CCl>CO.Cl>[ClH:56].[CH2:1]([C:3]1[N:12]=[C:11]([CH2:13][CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:53]([NH2:55])=[O:54])[C:7](=[O:52])[N:8]2[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[CH:18][CH:17]=1)[CH3:2]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 19093751HCID 19093751, compound

Product 1

HCID 178435360HCID 178435360, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

5,7-diethyl-2-oxo-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxamide (A) (500 mg) was dissolved in a mixture of methanol (5 ml), dichloromethane (3 ml) and concentrated hydrochloric acid (0.7 ml) and the mixture was stirred for 30 minutes. Volatile material was removed by evaporation and the residue was dissolved in a minimum of methanol. Ether was added to precipitate a solid which was collected by filtration. The solid was recrystallised from acetonitrile/methanol to give 5,7-diethyl-2-oxo-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]-1,2-dihydro-1,6-naphthyridin-3-carboxamide hydrochloride (220 mg), m.p. 264° C. (dec); NMR (d6 -DMSO+d4 -acetic acid): 1.29(t, 3H), 1.39(t, 3H), 3.02(q, 2H), 3.42(q, 2H), 5.66(s, 2H), 7.1(d, 2H), 7.25(d, 2H), 7.45-7.75(complex m, 5H), 9.03(s, 1H), mass spectrum (+ve FAB, methanol/DMSO/NBA): 480 (M+H)+ ; microanalysis, found: C, 61.7; H, 4.9; N, 18.7%; C27H25N7O2HCl.0.5H2O requires: C, 61.7; H, 4.9; N, 18.6%.

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in a minimum of methanol
  3. additionEther was added
  4. customto precipitate a solid which
  5. filtrationwas collected by filtration
  6. customThe solid was recrystallised from acetonitrile/methanol

Sources & evidence

ORD record
ord-8a822723f6d34bd09cef44a28a6ac963
Source dataset
uspto-grants-1993_06
Patent number
US05217976

Reaction notes

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