1,4-Dioxane hydrochloride → HCID 67503792, compound

HRID 1047059Notes

Reaction equation

HRID 1047059 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[N:10]=[C:11]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]4[N:22]=[CH:23][CH:24]=[CH:25][C:13]=4[N:12]3[C:26]=2[C:27]2[CH:32]=[CH:31][C:30]([C:33]3([NH:37]C(=O)OC(C)(C)C)[CH2:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[ClH:45].O1CCOCC1>C(Cl)Cl>[ClH:45].[ClH:45].[ClH:45].[ClH:45].[NH2:37][C:33]1([C:30]2[CH:29]=[CH:28][C:27]([C:26]3[N:12]4[C:13]5[CH:25]=[CH:24][CH:23]=[N:22][C:14]=5[NH:15][C:16]5[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=5[C:11]4=[N:10][C:9]=3[C:4]3[CH:5]=[CH:6][C:7]([CH3:8])=[C:2]([CH:3]=3)[NH2:1])=[CH:32][CH:31]=2)[CH2:34][CH2:35][CH2:36]1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087702HCID 69087702, compound

Product 1

HCID 67503792HCID 67503792, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(3-amino-4-methylphenyl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (28.2 mg, 0.0482 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 2 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (30.2 mg, 99.3%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.86-8.70 (m, 2H), 8.63 (s, 1H), 8.11 (dd, J=4.8, 1.4 Hz, 1H), 7.92 (dd, J=8.0, 1.8 Hz, 1H), 7.70-7.64 (m, 1H), 7.57-7.52 (m, 2H), 7.41-7.35 (m, 1H), 7.35-7.28 (m, 3H), 7.19-7.10 (m, 3H), 6.91 (dd, J=8.0, 1.4 Hz, 1H), 6.75 (dd, J=8.0, 4.8 Hz, 1H), 2.64-2.37 (m, 4H), 2.30 (s, 3H), 2.26-2.13 (m, 1H), 1.89-1.75 (m, 1H); LCMS: 485 [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-f508c5f0c11548a19683cad7939ab928
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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