1,4-Dioxane hydrochloride → 1-[4-(2-isoquinolin-6-yl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutanamine tetrahydrochloride

HRID 1047063Notes

Reaction equation

HRID 1047063 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:12]=[C:13]4[C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[NH:17][C:16]5[N:24]=[CH:25][CH:26]=[CH:27][C:15]=5[N:14]4[C:28]=3[C:29]3[CH:34]=[CH:33][C:32]([C:35]4([NH:39]C(=O)OC(C)(C)C)[CH2:38][CH2:37][CH2:36]4)=[CH:31][CH:30]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[ClH:47].O1CCOCC1>CO>[ClH:47].[ClH:47].[ClH:47].[ClH:47].[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:12]=[C:13]4[C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[NH:17][C:16]5[N:24]=[CH:25][CH:26]=[CH:27][C:15]=5[N:14]4[C:28]=3[C:29]3[CH:30]=[CH:31][C:32]([C:35]4([NH2:39])[CH2:38][CH2:37][CH2:36]4)=[CH:33][CH:34]=3)=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68067390tert-Butyl {1-[4-(2-isoquinolin-6-yl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate

Product 1

HCID 675038561-[4-(2-isoquinolin-6-yl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutanamine tetrahydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl {1-[4-(2-isoquinolin-6-yl-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (40 mg, 0.066 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 19 hours. The mixture was concentrated to afford the desired product (40 mg, 90%) as a yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.76 (br s, 2H), 8.69 (s, 1H), 8.60 (d, J=6.3 Hz, 1H), 8.36 (s, 1H), 8.33-8.28 (m, 2H), 8.14 (dd, J=4.6 Hz and 1.7 Hz, 1H), 8.04 (dd, J=8.0 Hz and 1.7 Hz, 1H), 7.92 (d, J=7.4 Hz, 1H), 7.62 (d, J=8.6 Hz, 2H), 7.45-7.40 (m, 2H), 7.33 (d, J=8.6 Hz, 1H), 7.18 (td, J=7.4 Hz and 1.1 Hz, 1H), 6.98 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.77 (dd, J=8.0 Hz and 4.6 Hz, 1H), 2.65-2.58 (m, 3H), 2.26-2.19 (m, 2H), 1.90-1.81 (m, 2H). LCMS: 507 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-5dc8b115cf2b4b53886842a30d832a7b
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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