1,4-Dioxane hydrochloride → HCID 67503632, compound

HRID 1047014Notes

Reaction equation

HRID 1047014 reaction equation
[C:1]([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(=O)OC(C)(C)C)[CH2:38][CH2:37][CH2:36]3)=[CH:31][CH:30]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[ClH:47].O1CCOCC1>C(Cl)Cl>[ClH:47].[ClH:47].[ClH:47].[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:1](=[O:3])[CH3:2])=[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 69087652HCID 69087652, compound

Product 1

HCID 67503632HCID 67503632, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(4-acetamidophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (22.6 mg, 0.0369 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 6 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (21.5 mg, 93.5%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 10.08 (s, 1H), 8.70 (br s, 2H), 8.64 (s, 1H), 8.11 (dd, J=4.8, 1.6 Hz, 1H), 7.95 (dd, J=7.8, 1.8 Hz, 1H), 7.58-7.49 (m, 4H), 7.44-7.36 (m, 3H), 7.34-7.28 (m, 3H), 7.17-7.10 (m, 1H), 6.89 (dd, J=8.0, 1.6 Hz, 1H), 6.75 (dd, J=7.8, 4.6 Hz, 1H), 2.65-2.39 (m, 4H), 2.26-2.13 (m, 1H), 2.04 (s, 3H), 1.89-1.75 (m, 1H); LCMS: 513 [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-ed1a93a1053a49c7b7a30e2a7bbf8533
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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