1,4-Dioxane hydrochloride → HCID 67504612, compound

HRID 1047081Notes

Reaction equation

HRID 1047081 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:14]=[C:15]4[C:21]5[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=5[NH:19][C:18]5[N:26]=[CH:27][CH:28]=[CH:29][C:17]=5[N:16]4[C:30]=3[C:31]3[CH:36]=[CH:35][C:34]([C:37]4([NH:41]C(=O)OC(C)(C)C)[CH2:40][CH2:39][CH2:38]4)=[CH:33][CH:32]=3)=[CH:9][CH:8]=2)=[O:5])[CH2:3][CH2:2]1.[ClH:49].O1CCOCC1>C(Cl)Cl>[ClH:49].[ClH:49].[ClH:49].[NH2:41][C:37]1([C:34]2[CH:33]=[CH:32][C:31]([C:30]3[N:16]4[C:17]5[CH:29]=[CH:28][CH:27]=[N:26][C:18]=5[NH:19][C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=5[C:15]4=[N:14][C:13]=3[C:10]3[CH:9]=[CH:8][C:7]([NH:6][C:4]([CH:1]4[CH2:3][CH2:2]4)=[O:5])=[CH:12][CH:11]=3)=[CH:36][CH:35]=2)[CH2:40][CH2:39][CH2:38]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087703HCID 69087703, compound

Product 1

HCID 67504612HCID 67504612, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl {1-[4-(2-{4-[(cyclopropylcarbonyl)amino]phenyl}-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl)phenyl]cyclobutyl}carbamate (53.9 mg, 0.0965 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 (48.8 mg, 78.1%) as yellow solid. 1HNMR (DMSO-d6) 500 MHz δ: 10.36 (s, 1H), 8.71-8.63 (m, 3H), 8.13-8.10 (m, 1H), 7.97-7.93 (m, 1H), 7.58-7.52 (m, 4H), 7.43-7.37 (m, 3H), 7.34-7.29 (m, 3H), 7.17-7.12 (m, 1H), 6.92-6.88 (m, 1H), 6.75 (dd, J=8.3, 4.9 Hz, 1H), 2.63-2.40 (m, 4H), 2.25-2.12 (m, 1H), 1.86-1.76 (m, 2H), 0.81-0.75 (m, 4H); LCMS: 539 [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-6ba83c2d9a5245b0a8a887801091d460
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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