1,4-Dioxane hydrochloride → HCID 69087688, compound

HRID 1047075Notes

Reaction equation

HRID 1047075 reaction equation
[CH3:1][O:2][C:3](=[O:47])[NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[NH:17][C:16]4[N:24]=[CH:25][CH:26]=[CH:27][C:15]=4[N:14]3[C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([C:35]3([NH:39]C(OC(C)(C)C)=O)[CH2:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)=[CH:7][CH:6]=1.Cl.O1CCOCC1>CO>[NH2:39][C:35]1([C:32]2[CH:33]=[CH:34][C:29]([C:28]3[N:14]4[C:15]5[CH:27]=[CH:26][CH:25]=[N:24][C:16]=5[NH:17][C:18]5[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=5[C:13]4=[N:12][C:11]=3[C:8]3[CH:7]=[CH:6][C:5]([NH:4][C:3](=[O:47])[O:2][CH3:1])=[CH:10][CH:9]=3)=[CH:30][CH:31]=2)[CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087704HCID 69087704, compound

Product 1

HCID 69087688HCID 69087688, compoundYield 132.4%

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]phenyl}carbamate (41 mg, 0.050 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 24 hours. The mixture was concentrated to afford the desired product (35 mg, 83%) as a yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 9.79 (s, 1H), 8.79-8.73 (m, 3H), 8.14 (dd, J=4.0 Hz and 1.7 Hz, 1H), 7.96 (dd, J=8.0 Hz and 1.1 Hz, 1H), 7.56 (d, J=8.0 Hz, 2H), 7.44-7.40 (m, 4H), 7.34-7.30 (m, 3H), 7.17 (t, J=7.2 Hz, 1H), 6.91 (dd, J=8.0 Hz and 1.1 Hz, 1H), 6.78 (dd, J=8.0 Hz and 4.6 Hz, 1H), 3.66 (s, 3H), 2.57 (t, J=7.7 Hz, 4H), 2.24-2.16 (m, 1H), 1.85-1.78 (m, 1H). LCMS: 529 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-0c5ad83f0c554f3e87b73771e9e2dc36
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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