1,4-Dioxane hydrochloride → HCID 67503754, compound

HRID 1047051Notes

Reaction equation

HRID 1047051 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]4[N:21]=[CH:22][CH:23]=[CH:24][C:12]=4[N:11]3[C:25]=2[C:26]2[CH:31]=[CH:30][C:29]([C:32]3([NH:36]C(=O)OC(C)(C)C)[CH2:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)=[CH:4][CH:3]=1.Cl.O1CCOCC1>CO>[NH2:36][C:32]1([C:29]2[CH:28]=[CH:27][C:26]([C:25]3[N:11]4[C:12]5[CH:24]=[CH:23][CH:22]=[N:21][C:13]=5[NH:14][C:15]5[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=5[C:10]4=[N:9][C:8]=3[C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)=[CH:31][CH:30]=2)[CH2:33][CH2:34][CH2:35]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087674HCID 69087674, compound

Product 1

HCID 67503754HCID 67503754, compoundYield 116.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (1-{4-[2-(4-hydroxyphenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (34 mg, 0.060 mmol) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 34 hours. The mixture was concentrated to afford the desired product (33 mg, 96%) as a brown solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.71-8.67 (m, 3H), 8.13 (dd, J=4.6, 1.4 Hz, 1H), 7.94 (dd, J=8.0, 1.4 Hz, 1H), 7.53 (d, J=9.7 Hz, 2H), 7.41 (t, J=7.7 Hz, 1H), 7.32-7.28 (m, 4H), 7.15 (t, J=7.4 Hz, 1H), 6.89 (dd, J=8.6, 1.7 Hz, 1H), 6.76 (dd, J=8.6, 4.6 Hz, 1H), 6.72 (d, J=8.6 Hz, 1H), 3.73-3.65 (m, 1H), 3.51-3.45 (m, 1H), 2.60-2.53 (m, 2H), 2.23-2.14 (m, 1H), 1.86-1.78 (m, 1H). LCMS: 472 [M+H].

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-3ec8905c625c4b2e9fe084a6e202e07f
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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