1,4-Dioxane hydrochloride → HCID 67503139, compound

HRID 1047010Notes

Reaction equation

HRID 1047010 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]([S:42]([CH3:45])(=[O:44])=[O:43])=[CH:38][CH:37]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1>CO>[CH3:45][S:42]([C:39]1[CH:40]=[CH:41][C:36]([C:19]2[N:20]=[C:21]3[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=4[NH:25][C:24]4[N:32]=[CH:33][CH:34]=[CH:35][C:23]=4[N:22]3[C:18]=2[C:15]2[CH:14]=[CH:13][C:12]([C:8]3([NH2:7])[CH2:11][CH2:10][CH2:9]3)=[CH:17][CH:16]=2)=[CH:37][CH:38]=1)(=[O:43])=[O:44]

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 69087719HCID 69087719, compound

Product 1

HCID 67503139HCID 67503139, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl[1-(4-{2-[4-(methylsulfonyl)phenyl]-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl}phenyl)cyclobutyl]carbamate (51 mg) in MeOH (0.5 mL) was added 4N HCl-dioxane (2 mL) and stirred at room temperature for 23 hours. The mixture was concentrated, then sat.NaHCO3 aq. was added. The mixture was extracted with AcOEt+MeOH, dried over Na2SO4, then filtrated through Celite pad. The filtrate was concentrated to afford the desired product (37 mg, 72%, 2 steps) as a pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.60 (s, 1H), 8.09 (dd, J=4.6 Hz and 1.7 Hz, 1H), 7.98 (dd, J=8.0 Hz and 1.7 Hz, 1H), 7.84 (d, J=8.6 Hz, 2H), 7.73 (d, J=8.6 Hz, 2H), 7.52 (d, J=8.0 Hz, 2H), 7.37 (td, J=7.4 Hz and 1.7 Hz, 1H), 7.30 (d, J=7.4 Hz, 1H), 7.24 (d, J=8.6 Hz, 2H), 7.14 (td, J=7.4 Hz and 1.7 Hz, 2H), 6.92 (dd, J=8.0 Hz and 1.7 Hz, 1H), 6.74 (dd, J=8.0 Hz and 5.2 Hz, 1H), 3.21 (s, 3H), 2.45-2.39 (m, 2H), 2.18-2.13 (m, 2H), 2.08-2.00 (m, 1H), 1.75-1.67 (m, 1H). LCMS: 534 [M+H].

Workup

  1. concentrationThe mixture was concentrated
  2. additionNaHCO3 aq. was added
  3. extractionThe mixture was extracted with AcOEt+MeOH
  4. dry with materialdried over Na2SO4
  5. filtrationfiltrated through Celite pad
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f2daf0acc4ef4610af6a52af77f7b504
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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