1,4-Dioxane hydrochloride → HCID 67503410, compound

HRID 1047008Notes

Reaction equation

HRID 1047008 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]4[N:23]=[CH:24][CH:25]=[CH:26][C:14]=4[N:13]3[C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([C:34]3([NH:38]C(=O)OC(C)(C)C)[CH2:37][CH2:36][CH2:35]3)=[CH:30][CH:29]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[ClH:46].O1CCOCC1>CO>[ClH:46].[ClH:46].[ClH:46].[NH2:38][C:34]1([C:31]2[CH:30]=[CH:29][C:28]([C:27]3[N:13]4[C:14]5[CH:26]=[CH:25][CH:24]=[N:23][C:15]=5[NH:16][C:17]5[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=5[C:12]4=[N:11][C:10]=3[C:7]3[CH:6]=[CH:5][C:4]([C:1](=[O:3])[CH3:2])=[CH:9][CH:8]=3)=[CH:33][CH:32]=2)[CH2:35][CH2:36][CH2:37]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68067214HCID 68067214, compound

Product 1

HCID 67503410HCID 67503410, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (1-{4-[2-(4-acetylphenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (27 mg, 0.045 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 22.5 hours. The mixture was concentrated to afford the desired product (27 mg, 98%) as a pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.66-8.63 (m, 3H), 8.11 (dd, J=4.6 Hz and 1.7 Hz, 1H), 7.98 (dd, J=8.0 Hz and 1.7 Hz, 1H), 7.88 (d, J=8.6 Hz, 2H), 7.61 (d, J=8.6 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 7.35-7.35 (m, 2H), 7.31 (d, J=7.4 Hz, 1H), 7.14 (t, J=7.2 Hz, 1H), 6.91 (dd, J=8.0 Hz and 1.7 Hz, 1H), 6.74 (dd, J=8.0 Hz and 4.6 Hz, 1H), 3.73-3.70 (m, 1H), 3.68-3.65 (m, 1H), 2.64-2.53 (m, 5H), 2.24-2.15 (m, 1H), 1.89-1.80 (m, 1H). LCMS: 498 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-8cb2229926514cf190c5f9401f4b769d
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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