1,4-Dioxane hydrochloride → HCID 67502938, compound

HRID 1047030Notes

Reaction equation

HRID 1047030 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[NH:18][C:17]4[N:25]=[CH:26][CH:27]=[CH:28][C:16]=4[N:15]3[C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([C:36]3([NH:40]C(=O)OC(C)(C)C)[CH2:39][CH2:38][CH2:37]3)=[CH:32][CH:31]=2)=[CH:8][CH:7]=1)(=[O:4])=[O:3].[ClH:48].O1CCOCC1>C(Cl)Cl>[ClH:48].[ClH:48].[ClH:48].[NH2:40][C:36]1([C:33]2[CH:32]=[CH:31][C:30]([C:29]3[N:15]4[C:16]5[CH:28]=[CH:27][CH:26]=[N:25][C:17]=5[NH:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=5[C:14]4=[N:13][C:12]=3[C:9]3[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][CH:10]=3)=[CH:35][CH:34]=2)[CH2:39][CH2:38][CH2:37]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087653HCID 69087653, compound

Product 1

HCID 67502938HCID 67502938, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {1-[4-(2-{4-[(methylsulfonyl)amino]phenyl}-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (30.9 mg, 0.0476 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 13.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (24.4 mg, 77.9%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 9.90 (s, 1H), 8.76 (br s, 2H), 8.67 (s, 1H), 8.12 (dd, J=4.8, 1.6 Hz, 1H), 7.95 (dd, J=8.0, 1.6 Hz, 1H), 7.59-7.53 (m, 2H), 7.49-7.45 (m, 2H), 7.43-7.37 (m, 1H), 7.36-7.29 (m, 3H), 7.18-7.11 (m, 3H), 6.90 (dd, J=8.0, 1.6 Hz, 1H), 6.76 (dd, J=8.0, 4.8 Hz, 1H), 3.02 (s, 3H), 2.62-2.53 (m, 4H), 2.27-2.13 (m, 1H), 1.88-1.75 (m, 1H); LCMS: 549 [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-6f5e4fc509244f98b75951d5f08eaa2d
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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