1,4-Dioxane hydrochloride → 1-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochloride

HRID 1047069Notes

Reaction equation

HRID 1047069 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:33]=[CH:32][C:31]([C:34]2([NH:38]C(=O)OC(C)(C)C)[CH2:37][CH2:36][CH2:35]2)=[CH:30][CH:29]=1.[ClH:46].O1CCOCC1>C(Cl)Cl>[ClH:46].[ClH:46].[ClH:46].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[N:11]=[C:12]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[NH:16][C:15]3[N:23]=[CH:24][CH:25]=[CH:26][C:14]=3[N:13]2[C:27]=1[C:28]1[CH:29]=[CH:30][C:31]([C:34]2([NH2:38])[CH2:37][CH2:36][CH2:35]2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86664673tert-Butyl (1-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate

Product 1

HCID 675034241-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutanamine trihydrochlorideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (1-{4-[2-(1,3-benzoxazol-2-yl)-9H-imidazo[1,2-d]pyrido[2,3-b][1,4]benzodiazepin-3-yl]phenyl}cyclobutyl)carbamate (11.3 mg, 0.0189 mmol) was dissolved in DCM (1 mL). 4M HCl/dioxane (1 mL) was added to the mixture and stirred at room temperature for 17.5 hours. The mixture was concentrated and solidified with ether. The precipitated solids were collected by filtration and washed with ether to afford desired product (10.6 mg, 92.7%) as pale yellow solid. 1HNMR (DMSO-d6) 400 MHz δ: 8.73 (s, 1H), 8.67 (br s, 3H), 8.16 (dd, J=4.8, 1.6 Hz, 1H), 8.00 (dd, J=7.9, 1.6 Hz, 1H), 7.75-7.71 (m, 1H), 7.68-7.64 (m, 1H), 7.63-7.49 (m, 4H), 7.46-7.31 (m, 4H), 7.21-7.13 (m, 1H), 6.95 (dd, J=7.9, 1.6 Hz, 1H), 6.77 (dd, J=7.9, 4.8 Hz, 1H), 2.70-2.43 (m, 4H), 2.27-2.13 (m, 1H), 1.93-1.78 (m, 1H); LCMS: 497 [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-1480a6f2ba214976ac248ee7310aaedf
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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