Hydrochloric Acid → N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide hydrochloride

HRID 1778100Notes

Reaction equation

HRID 1778100 reaction equation
[ClH:1].[C:2]([C:4]1[C:5]([NH:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH2:28][N:29]4[CH2:34][CH2:33][NH:32][CH2:31][C:30]4=[O:35])=[C:20]([CH:23](OC)[O:24]C)[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3]>C1COCC1.O>[ClH:1].[C:2]([C:4]1[C:5]([NH:36][CH2:37][CH2:38][O:39][CH3:40])=[CH:6][C:7]([NH:10][C:11]([N:13]2[C:22]3[C:17](=[CH:18][C:19]([CH2:28][N:29]4[CH2:34][CH2:33][NH:32][CH2:31][C:30]4=[O:35])=[C:20]([CH:23]=[O:24])[N:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[N:8][CH:9]=1)#[N:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118036955HCID 118036955, compound2×

Product 1

HCID 118036805N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-formyl-6-((2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide hydrochloride

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Concentrated hydrochloric acid (0.31 ml) was added to a solution of N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-((2-oxopiperazin-1-yl)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 121, 250 mg, 0.371 mmol) in THF (10 ml) and water (2 ml) at room temperature. After stirring for 18 h at room temperature the reaction mixture was evaporated. The residue was purified by reversed phase HPLC (RP 2) to give the title compound.

Workup

  1. customwas evaporated
  2. customThe residue was purified by reversed phase HPLC (RP 2)

Sources & evidence

ORD record
ord-c93cd41803c2484d98245b602f89768e
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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