Hydrazine hydrate (1:1) → HCID 69069753, compound

HRID 216138Notes

Reaction equation

HRID 216138 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([NH:17][CH2:18][CH2:19][C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:27])[N:14]=[C:13]([O:28][CH3:29])[N:12]=2)[CH:8]=[CH:7][C:6]1=[O:30].O.[NH2:33][NH2:34]>CO.C(Cl)Cl>[Cl:27][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([F:26])[C:20]=1[CH2:19][CH2:18][NH:17][C:15]1[N:14]=[C:13]([O:28][CH3:29])[N:12]=[C:11]([C:9]2[CH:8]=[CH:7][C:6](=[O:30])[N:5]([CH2:4][C:3]([NH:33][NH2:34])=[O:2])[CH:10]=2)[CH:16]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 11640888HCID 11640888, compound

Product 1

HCID 69069753HCID 69069753, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of (5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-2-oxo-2H-pyridin-1-yl)-acetic acid methyl ester [220 mg, 0.49 mmol, Example 22(d)] in a mixture of MeOH (5 mL) and DCM (2 mL) is treated with hydrazine hydrate (0.18 mL, 5.8 mmol). After 15 hours at 20° C., the mixture is concentrated to give (5-{6-[2-(2-chloro-6-fluoro-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-2-oxo-2H-pyridin-1-yl)-acetic acid hydrazide. MS: 447 (M+H). This material is used without further purification.

Workup

  1. concentrationthe mixture is concentrated

Sources & evidence

ORD record
ord-5a61c5f8357d4bcfa695898bde60f057
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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