Hydrochloric Acid → HCID 86669250, compound

HRID 2366912Notes

Reaction equation

CC([CH:5]1[CH2:10][N:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28](=[O:30])[CH3:29])[C@@H:23]([CH3:31])[CH2:22][C@H:21]4[NH:32][C:33]([O:35][CH:36]([CH3:38])[CH3:37])=[O:34])=[CH:14][CH:13]=2)[CH2:8][CH2:7][N:6]1C([O-])=O)(C)C.[ClH:42]>CO>[ClH:42].[ClH:42].[C:28]([N:24]1[C:25]2[C:20](=[CH:19][C:18]([C:15]3[CH:16]=[CH:17][C:12]([CH2:11][N:9]4[CH2:8][CH2:7][NH:6][CH2:5][CH2:10]4)=[CH:13][CH:14]=3)=[CH:27][CH:26]=2)[C@H:21]([NH:32][C:33](=[O:34])[O:35][CH:36]([CH3:37])[CH3:38])[CH2:22][C@@H:23]1[CH3:31])(=[O:30])[CH3:29]

Participants

Conditions

Temperature: 70 °C

Procedure

1,1-Dimethylethyl-4-({-4-[(cis)-1-acetyl-2-methyl-4-({[(1-methylethyl)oxy]carbonyl}amino)-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)-1-piperazinecarboxylate (for a preparation see Intermediate 8) (98 mg, 0.174 mmol) was dissolved in methanol (2 mL) and to this was added 1.25M HCl in methanol. (0.305 mL, 0.382 mmol) and stirred overnight. 1.25M HCl in methanol. (0.305 mL, 0.382 mmol) was added and the reaction was heated in a sealed vessel to 70° C. in an optimiser microwave for 15 min followed by a further 30 min. 2 eqv of 1.25M HCl in methanol was added and the reaction mixture heated in the microwave under the same conditions for a further 1 hr. The reaction mixture was reduced in vacuo to give a white solid (86 mg). LCMS (Method A): Rt=0.92, MH+=465

Workup

addition(0.305 mL, 0.382 mmol) was added
waitfollowed by a further 30 min
temperaturethe reaction mixture heated in the microwave under the same conditions for a further 1 hr

Sources & evidence

ORD record: ord-d04398dcef9d458fb171a6ad5c69c3ad
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697725B2

Reaction notes

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