1,4-Dioxane hydrochloride → HCID 67503098, compound

HRID 1047078Notes

Reaction equation

HRID 1047078 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]4[C:23]5[CH:35]=[CH:34][CH:33]=[N:32][C:24]=5[NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:21]4=[N:20][C:19]=3[C:36]3[CH:41]=[CH:40][C:39]([N:42]4[CH2:47][CH2:46][CH2:45][CH2:44][C:43]4=[O:48])=[CH:38][CH:37]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.[ClH:50].O1CCOCC1>C(Cl)Cl>[ClH:50].[ClH:50].[ClH:50].[NH2:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:22]4[C:23]5[CH:35]=[CH:34][CH:33]=[N:32][C:24]=5[NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[C:21]4=[N:20][C:19]=3[C:36]3[CH:37]=[CH:38][C:39]([N:42]4[CH2:47][CH2:46][CH2:45][CH2:44][C:43]4=[O:48])=[CH:40][CH:41]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087689HCID 69087689, compound

Product 1

HCID 67503098HCID 67503098, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl[1-(4-{2-[4-(2-oxopiperidin-1-yl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutyl]carbamate (31.9 mg, 0.0489 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 19 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (27.2 mg, 84.1%) as yellow solid. 1HNMR (DMSO-d6) 500 MHz δ: 8.80-8.69 (m, 3H), 8.65 (br s, 1H), 8.13-8.09 (m, 1H), 7.98-7.93 (m, 1H), 7.59-7.54 (m, 2H), 7.51-7.47 (m, 2H), 7.41-7.29 (m, 4H), 7.25-7.21 (m, 2H), 7.16-7.11 (m, 1H), 6.93-6.88 (m, 1H), 6.75 (dd, J=7.7, 4.9 Hz, 1H), 3.62-3.57 (m, 2H), 2.62-2.47 (m, 4H), 2.41-2.35 (m, 2H), 2.24-2.13 (m, 1H), 1.90-1.78 (m, 5H); LCMS: 553 [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-cdfc00e594ff4bdfa648982223517458
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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