1,4-Dioxane hydrochloride → 1-(4-{2-[4-(morpholin-4-ylmethyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutanamine tetrahydrochloride

HRID 1047004Notes

Reaction equation

HRID 1047004 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]4[C:23]5[CH:35]=[CH:34][CH:33]=[N:32][C:24]=5[NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:21]4=[N:20][C:19]=3[C:36]3[CH:41]=[CH:40][C:39]([CH2:42][N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)=[CH:38][CH:37]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.[ClH:50].O1CCOCC1>CO>[ClH:50].[ClH:50].[ClH:50].[ClH:50].[N:43]1([CH2:42][C:39]2[CH:40]=[CH:41][C:36]([C:19]3[N:20]=[C:21]4[C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[NH:25][C:24]5[N:32]=[CH:33][CH:34]=[CH:35][C:23]=5[N:22]4[C:18]=3[C:15]3[CH:14]=[CH:13][C:12]([C:8]4([NH2:7])[CH2:11][CH2:10][CH2:9]4)=[CH:17][CH:16]=3)=[CH:37][CH:38]=2)[CH2:44][CH2:45][O:46][CH2:47][CH2:48]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087640tert-butyl[1-(4-{2-[4-(morpholin-4-ylmethyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutyl]carbamate

Product 1

HCID 675042701-(4-{2-[4-(morpholin-4-ylmethyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutanamine tetrahydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-butyl[1-(4-{2-[4-(morpholin-4-ylmethyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutyl]carbamate (28 mg, 0.043 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at r.t for 15 hours. The mixture was concentrated to afford the desired product (31 mg, quant) as a yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.74 (br s, 2H), 8.61 (s, 1H), 8.10 (dd, J=4.9 Hz and 1.4 Hz, 1H), 7.96 (dd, J=7.7 Hz and 1.4 Hz, 1H), 7.59 (dd, J=15.5 Hz and 8.6 Hz, 4H), 7.53 (d, J=8.6 Hz, 2H), 7.36 (d, J=7.4 Hz, 3H), 7.30 (dd, J=7.4 Hz and 1.1 Hz, 1H), 7.13 (td, J=7.4 Hz and 1.1 Hz, 1H), 6.88 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.73 (dd, J=7.4 Hz and 4.9 Hz, 1H), 5.76 (s, 2H), 4.30 (d, J=5.2 Hz, 2H), 3.94 (dd, J=12.0 Hz and 2.3 Hz, 2H), 3.22 (d, J=11.5 Hz, 2H), 3.11-3.04 (m, 2H), 2.59-2.55 (m, 4H), 2.24-2.16 (m, 1H), 1.87-1.78 (m, 1H). LCMS: 555 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-50878488f0dc41db9e284820d5c4531d
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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