Dimethylamine → HCID 59212488, compound

HRID 2243861Notes

Reaction equation

HRID 2243861 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1.[CH3:31][NH:32][CH3:33]>CN1C(=O)CCC1.CO>[CH3:31][N:32]([CH3:33])[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:14]3[CH:15]=[C:16]([NH:21][C:22]([NH:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:23])[CH:17]=[CH:18][C:19]=3[CH3:20])[C:8](=[O:13])[N:9]2[CH3:12])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 59212456HCID 59212456, compound

Product 1

HCID 59212488HCID 59212488, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

1-(3-(7-chloro-1,2-dihydro-1-methyl-2-oxo-1,6-naphthyridin-3-yl)-4-methylphenyl)-3-phenylurea A6 (50 mg, 0.12 mmol) is dissolved in NMP (1 mL) and treated with dimethyl amine (0.60 mL of a 2.0 M solution in methanol). The reaction mixture is heated to 100° C. for 12 h. Upon cooling to rt the reaction is purified by preparative LCMS. 1H NMR 400 MHz (DMSO-d6) δ 8.65 (s, 1H), 8.62 (s, 1H), 8.50 (s, 1H), 7.75 (s, 1H), 7.45-7.42 (m, 2H), 7.38 (d, J=2 Hz, 1H), 7.29-7.25 (m, 3H), 7.15 (d, J=8 Hz, 1H), 6.96 (m, 1H), 6.37 (s, 1H), 3.60 (s, 3H), 3.19 (s, 6H), 2.08 (s, 3H); MS m/z 428.2 (M+1).

Workup

  1. temperatureUpon cooling to rt the reaction
  2. customis purified by preparative LCMS

Sources & evidence

ORD record
ord-61f1741553594b2190e26411e85199d4
Source dataset
uspto-grants-2010_03
Patent number
US07678792B2

Reaction notes

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