Hydrochloric Acid → HCID 67271849, compound

HRID 1696583Notes

Reaction equation

[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:46])[NH:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH2:23][N:22](C(OC(C)(C)C)=O)[CH:21]([C:34]([O:36]CC)=[O:35])[CH2:20]3)[N:15]=[C:14]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])[CH:13]=1.Cl>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:46])[NH:11][C:12]1[N:16]([C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[CH2:23][NH:22][CH:21]([C:34]([OH:36])=[O:35])[CH2:20]3)[N:15]=[C:14]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[F:45])[CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 2-t-butyl 3-ethyl 6-(5-(3-(2,3-dichlorophenyl)ureido)-3-(2-fluorophenyl)-1H-pyrazol-1-yl)-3,4-dihydroisoquinoline-2,3(1H)-dicarboxylate (0.050 g, 0.075 mmol) in THF (2 mL) was added 6N HCl (2 mL) and the solution was stirred at 50° C. overnight. The organic solvent was evaporated and the precipitate was collected to yield 6-(5-(3-(2,3-dichlorophenyl)ureido)-3-(2-fluorophenyl)-1H-pyrazol-1-yl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride as a white solid (15 mg, 35% yield). 1H-NMR (acetone-d6): δ 8.01-7.96 (m, 2H), 7.62-7.60 (m, 2H), 7.47 (d, 1H, J=8.0 Hz), 7.42-7.37 (m, 1H), 7.27-7.19 (m, 4H), 6.92 (d, 1H, J=3.6 Hz), 4.59 (d, 1H, J=16.0 Hz), 4.50 (d, 1H, J=16.0 Hz), 4.48 (dd, 1H, J=11.4, 5.0 Hz), 3.61 (dd, 1H, J=18.0, 5.2 Hz), urea, acid and amine protons not visible, one proton is buried under the methanol peak. LC-MS (EI) m/z: 540.0 542.0 (M+H+).

Workup

customThe organic solvent was evaporated
customthe precipitate was collected

Sources & evidence

ORD record: ord-aeb99a3def134344b6c00d30f747e124
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163756B2

Reaction notes

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