1,4-Dioxane hydrochloride → HCID 67504289, compound

HRID 1047016Notes

Reaction equation

HRID 1047016 reaction equation
[NH2:1][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.[ClH:44].O1CCOCC1>C(Cl)Cl>[ClH:44].[ClH:44].[ClH:44].[ClH:44].[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]([NH2:1])=[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 69087658HCID 69087658, compound

Product 1

HCID 67504289HCID 67504289, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(4-aminophenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (32.0 mg, 0.0561 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 (28.4 mg, 82.3%) as a pale red solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.78 (br s, 3H), 8.66 (br s, 1H), 8.12 (dd, J=4.8, 1.6 Hz, 1H), 7.95 (dd, J=7.8, 1.4 Hz, 1H), 7.59-7.53 (m, 2H), 7.52-7.46 (m, 2H), 7.43-7.36 (m, 1H), 7.35-7.28 (m, 3H), 7.22-7.09 (m, 3H), 6.90 (dd, J=8.0, 1.6 Hz, 1H), 6.76 (dd, J=8.0, 4.8 Hz, 1H), 2.61-2.53 (m, 4H), 2.27-2.13 (m, 1H), 1.89-1.75 (m, 1H); LCMS: 471 [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-c862ddfd756a4c9b9ed1cc6547fb6f95
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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