1,4-Dioxane hydrochloride → HCID 67504334, compound

HRID 1047044Notes

Reaction equation

HRID 1047044 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])=[C:39]([OH:47])[CH:38]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=O)(C)(C)C.Cl.O1CCOCC1>CO>[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:46]=[CH:45][C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([OH:47])[CH:38]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 67503395HCID 67503395, compound

Product 1

HCID 67504334HCID 67504334, compoundYield 108.9%

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]-2-hydroxybenzoate (33 mg, 0.052 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 13 hours. The mixture was concentrated to afford the desired product (30 mg, 90%) as a yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 10.48 (s, 1H), 8.64-8.62 (m, 3H), 8.10 (dd, J=4.9 Hz and 1.4 Hz, 1H), 7.96 (dd, J=8.0 Hz and 1.4 Hz, 1H), 7.69 (d, J=8.0 Hz, 1H), 7.57 (d, J=8.0 Hz, 1H), 7.39-7.36 (m, 2H), 7.30 (dd, J=8.0 Hz and 1.1 Hz, 1H), 7.15-7.06 (m, 2H), 6.89 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.73 (dd, J=8.0 Hz and 4.6 Hz, 1H), 3.88 (s, 3H), 3.51-3.45 (m, 2H), 2.64-2.52 (m, 2H), 2.23-2.15 (m, 1H), 1.88-1.81 (m, 1H). LCMS: 530 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-a231131dfb7340b38c82efadab3f38db
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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