Sodium Hydroxide → HCID 11741526, compound

HRID 1823400Notes

Reaction equation

HRID 1823400 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:33][CH2:34][CH2:35][CH3:36])[N:14]([CH2:15][CH2:16][NH:17][C:18]([CH:20]([NH:25]C(=O)OC(C)(C)C)[CH2:21][CH:22]([CH3:24])[CH3:23])=[O:19])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.[OH-].[Na+]>Cl>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:33][CH2:34][CH2:35][CH3:36])[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:19])[CH:20]([NH2:25])[CH2:21][CH:22]([CH3:24])[CH3:23])[C:10]=2[C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221726831,1-Dimethylethyl N-[1-({[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]amino}carbonyl)-3-methylbutyl]carbamate

Product 1

HCID 11741526HCID 11741526, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1,1-Dimethylethyl N-[1-({[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]amino}carbonyl)-3-methylbutyl]carbamate (0.35 g, 0.7 mmol) was combined with 1 N hydrochloric acid (40 mL) and heated on a steam bath for 30 minutes. The reaction mixture was allowed to cool and then it was made basic with 10% sodium hydroxide. The resulting precipitate was isolated by filtration and dried to provide 0.15 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-2-amino-4-methylpentamide as a white solid, m.p. 60–65° C. Analysis: Calculated for C21H31N7O: % C, 63.27; % H, 7.86; % N, 24.66; Found: % C, 62.27; % H, 7.67; % N, 24.77. HRMS (EI) calcd for C21H31N7O (M+) 397.2590 found 397.2582.

Workup

  1. temperatureheated on a steam bath for 30 minutes
  2. temperatureto cool
  3. customThe resulting precipitate was isolated by filtration
  4. customdried
  5. customto provide 0.15 g of N1-[2-(4-amino-2-butyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl)ethyl]-2-amino-4-methylpentamide as a white solid, m.p. 60–65° C

Sources & evidence

ORD record
ord-6a237fb7bcb747e280114f9299ad0741
Source dataset
uspto-grants-2006_05
Patent number
US07038051B2

Reaction notes

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