Hydrochloric Acid → HCID 86713644, compound

HRID 1430494Notes

Reaction equation

HRID 1430494 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:26])[N:10]([CH2:24][CH3:25])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][N:21]([CH3:23])[CH3:22])[CH:12]=3)=[CH:6][C:5]([NH:27][C:28]([NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:29])=[C:4]([F:37])[CH:3]=1.[ClH:38]>CO.CCOC(C)=O>[ClH:1].[ClH:38].[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:26])[N:10]([CH2:24][CH3:25])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][N:21]([CH3:22])[CH3:23])[CH:12]=3)=[CH:6][C:5]([NH:27][C:28]([NH:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:29])=[C:4]([F:37])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71584928HCID 71584928, compound

Product 1

HCID 86713644HCID 86713644, compoundYield 180.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(4-chloro-5-(7-(2-(dimethylamino)ethylamino)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (0.260 g, 0.497 mmol) in MeOH (1 mL) was added HCl (1.25 M in MeOH) (0.875 mL, 1.094 mmol) and the mixture was stirred at RT for 1 h. The reaction mixture was diluted with EtOAc and the remaining solid was filtered, washed and dried to provide 1-(4-chloro-5-(7-(2-(dimethylamino)ethylamino)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea dihydrochloride (267 mg, 90% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.37 (s, 1H), 8.83 (s, 1H), 8.44 (s, 1H), 8.17 (d, J=9 Hz, 1H), 7.78 (m, 1H), 7.52 (d, J=11 Hz, 1H), 7.42 (m, 2H), 7.25 (m, 3H), 6.95 (t, J=8 Hz, 1H), 6.42 (s, 1H), 4.13 (m, 2H), 3.63 (m, 2H), 3.02 (s, 2H), 2.64 (s, 6), 1.20 (t, J=6 Hz, 3H); MS (ESI) m/z: 523.2 [M+H]+.

Workup

  1. filtrationthe remaining solid was filtered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-d65efdd45849456ca9c70d02cb6eb296
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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