1,4-Dioxane hydrochloride → methyl 4-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}benzoate trihydrochloride

HRID 1047000Notes

Reaction equation

HRID 1047000 reaction equation
C(OC([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:23]4[C:24]5[CH:36]=[CH:35][CH:34]=[N:33][C:25]=5[NH:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:22]4=[N:21][C:20]=3[C:37]3[CH:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:39][CH:38]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.[ClH:47].O1CCOCC1>CO>[ClH:47].[ClH:47].[ClH:47].[NH2:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[N:23]4[C:24]5[CH:36]=[CH:35][CH:34]=[N:33][C:25]=5[NH:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=5[C:22]4=[N:21][C:20]=3[C:37]3[CH:38]=[CH:39][C:40]([C:41]([O:43][CH3:44])=[O:42])=[CH:45][CH:46]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67504209Methyl 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]benzoate

Product 1

HCID 67504041methyl 4-{3-[4-(1-aminocyclobutyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl}benzoate trihydrochlorideYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-[3-(4-{1-[(tert-butoxycarbonyl)amino]cyclobutyl}phenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-2-yl]benzoate (28 mg, 0.046 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 18 hours. The mixture was concentrated to afford the desired product (28 mg, 97%) as a yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.80 (s, 2H), 8.65 (s, 1H), 8.12 (dd, J=4.6 Hz and 1.7 Hz, 1H), 7.98 (dd, J=7.4 Hz and 1.7 Hz, 1H), 7.89-7.87 (m, 2H), 7.59 (dd, J=12.0 Hz and 8.6 Hz, 4H), 7.40-7.30 (m, 4H), 7.14 (t, J=7.2 Hz, 1H), 6.92 (dd, J=8.0 Hz and 1.7 Hz, 1H), 6.76 (dd, J=4.6 Hz and 4.6 Hz, 1H), 3.84 (s, 3H), 2.59 (t, J=7.4 Hz, 4H), 2.26-2.17 (m, 1H), 1.87-1.78 (m, 1H). LCMS: 514 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-51363dbbc6b94934b47e6c9ef2524bab
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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