6-Ethoxy-2-pyridinamine → Ethyl 6-ethoxy-4-(6-ethoxy-2-pyridylamino)-7-methyl-1,8-naphthyridine-3-carboxylate sesquihydrochloride hydrate

HRID 1956443Notes

Reaction equation

HRID 1956443 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[N:7][C:8]([CH3:15])=[C:9]([O:12][CH2:13][CH3:14])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH3:20])=[O:17].[NH2:21][C:22]1[N:27]=[C:26]([O:28][CH2:29][CH3:30])[CH:25]=[CH:24][CH:23]=1>Cl>[OH2:12].[ClH:1].[CH2:13]([O:12][C:9]1[CH:10]=[C:11]2[C:6](=[N:7][C:8]=1[CH3:15])[N:5]=[CH:4][C:3]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:2]2[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:28][CH2:29][CH3:30])[N:27]=1)[CH3:14].[ClH:1].[ClH:1].[CH2:19]([O:18][C:16]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[NH:21][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]([O:28][CH2:29][CH3:30])[N:27]=1)=[CH:10][C:9]([O:12][CH2:13][CH3:14])=[C:8]([CH3:15])[N:7]=2)=[O:17])[CH3:20].[OH2:12]

Participants

4

Reactant 2

HCID 5867106-Ethoxy-2-pyridinamineHCID 23198600Ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate

Product 1

HCID 131720767Ethyl 6-ethoxy-4-(6-ethoxy-2-pyridylamino)-7-methyl-1,8-naphthyridine-3-carboxylate sesquihydrochloride hydrate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A mixture of ethyl 4-chloro-6-ethoxy-7-methyl-1,8-naphthyridine-3-carboxylate (1.3 g), 6-amino-2-ethoxy pyridine (0.68 g), IMS (25 ml) and concentrated hydrochloric acid (2 drops) was boiled under reflux for 18 hours. The mixture was cooled and filtered to give ethyl 6-ethoxy-4-(6-ethoxy-2-pyridylamino)-7-methyl-1,8-naphthyridine-3-carboxylate sesquihydrochloride hydrate, m.p. 195°-200° C. Active (1/1) at 30 mg/kg.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered

Sources & evidence

ORD record
ord-745f2b90cee9427da243b8cfd4480318
Source dataset
uspto-grants-1998_07
Patent number
US05780482

Reaction notes

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