1,4-Dioxane hydrochloride → HCID 67503282, compound

HRID 1047006Notes

Reaction equation

HRID 1047006 reaction equation
[N+: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])=[O:2].[ClH:46].O1CCOCC1>C(Cl)Cl>[ClH:46].[ClH:46].[ClH:46].[N+: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:29]=[CH:30][C:31]([C:34]3([NH2:38])[CH2:37][CH2:36][CH2:35]3)=[CH:32][CH:33]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 68067477HCID 68067477, compound

Product 1

HCID 67503282HCID 67503282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(4-nitrophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (7.70 mg, 0.0128 mmol) was dissolved in DCM (0.5 mL). 4M HCl/dioxane (0.5 mL) was added to the mixture and stirred at room temperature for 4 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (8.04 mg, quant.) as an orange solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.72 (br s, 2H), 8.65 (s, 1H), 8.19-8.14 (m, 2H), 8.13-8.10 (m, 1H), 8.00-7.96 (m, 1H), 7.73-7.68 (m, 2H), 7.62-7.56 (m, 2H), 7.42-7.36 (m, 3H), 7.33-7.29 (m, 1H), 7.18-7.12 (m, 1H), 6.96-6.92 (m, 1H), 6.75 (dd, J=8.0, 4.8 Hz, 1H), 2.69-2.44 (m, 4H), 2.28-2.15 (m, 1H), 1.93-1.78 (m, 1H); LCMS: 501 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. filtrationThe precipitated solids were collected by filtration
  3. washwashed with ether

Sources & evidence

ORD record
ord-ace9cad22ed7425890c06caa07a07f27
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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