Hydrochloric Acid → HCID 86713645, compound

HRID 1430495Notes

Reaction equation

HRID 1430495 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:27])[N:10]([CH2:25][CH3:26])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:24])[CH3:23])[CH:12]=3)=[CH:6][C:5]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:30])=[C:4]([F:38])[CH:3]=1.[ClH:39]>CO.CCOC(C)=O>[ClH:1].[ClH:39].[Cl:1][C:2]1[C:7]([C:8]2[C:9](=[O:27])[N:10]([CH2:25][CH3:26])[C:11]3[C:16]([CH:17]=2)=[CH:15][N:14]=[C:13]([NH:18][CH2:19][CH2:20][CH2:21][N:22]([CH3:23])[CH3:24])[CH:12]=3)=[CH:6][C:5]([NH:28][C:29]([NH:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)=[O:30])=[C:4]([F:38])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71584929HCID 71584929, compound

Product 1

HCID 86713645HCID 86713645, compoundYield 159.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 1-(4-chloro-5-(7-(3-(dimethylamino)propylamino)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea (0.130 g, 0.242 mmol) in MeOH (1 mL) was added HCl (1.25 M in MeOH, 0.426 mL, 0.533 mmol) and the mixture stirred at RT for 1 h. The reaction mixture was diluted with EtOAc, filtered, washed and dried to provide 1-(4-chloro-5-(7-(3-(dimethylamino)propylamino)-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-2-fluorophenyl)-3-phenylurea dihydrochloride (118 mg, 80% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 9.44 (s, 1H), 8.86 (s, 1H), 8.43 (s, 1H), 8.17 (d, J=9 Hz, 1H), 7.76 (s, 1H), 7.52 (d, J=9 Hz, 1H), 7.42 (m, 2H), 7.25 (m, 3H), 6.96 (t, J=7 Hz, 1H), 6.34 (s, 1H), 4.12 (m, 2H), 3.42 (m, 2H), 3.10 (m, 2H), 2.75 (s, 6H), 1.93 (m, 2H), 1.18 (t, J=6 Hz, 3H); MS (ESI) m/z: 537.2. [M+H]+.

Workup

  1. filtrationfiltered
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-e1e748916d4a4abe946e8ec4c06d7a04
Source dataset
uspto-grants-2015_01
Patent number
US08940756B2

Reaction notes

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