Hydrochloric Acid → 3,9-bis-[2-(pyrrolidin-2-yl)-3H-imidazol-4-yl]-6-methyl-6,7-dihydro-5H-dibenzo[c,e]azepine

HRID 2038947Notes

Reaction equation

C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]3[C:27]4[CH:28]=[CH:29][C:30]([C:32]5[NH:33][C:34]([CH:37]6[CH2:41][CH2:40][CH2:39][N:38]6C(OC(C)(C)C)=O)=[N:35][CH:36]=5)=[CH:31][C:26]=4[CH2:25][N:24]([CH3:49])[CH2:23][C:22]=3[CH:50]=2)=[CH:15][N:14]=1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl.CO>[NH:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[NH:17][C:16]([C:18]2[CH:19]=[CH:20][C:21]3[C:27]4[CH:28]=[CH:29][C:30]([C:32]5[NH:33][C:34]([CH:37]6[CH2:41][CH2:40][CH2:39][NH:38]6)=[N:35][CH:36]=5)=[CH:31][C:26]=4[CH2:25][N:24]([CH3:49])[CH2:23][C:22]=3[CH:50]=2)=[CH:15][N:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To the solution of 3,9-bis-[2-(1-tert-butoxycarbonyl-pyrrolidin-2-yl)-3H-imidazol-4-yl]-6-methyl-6,7-dihydro-5H-dibenzo[c,e]azepine (24 mg) in DCM/MeOH (1.6 ml/0.75 ml) was added hydrochloric acid in dioxane (0.44 ml, 1.7 mmol). The mixture was heated at 50° C. for 3 hours and the solvents were evaporated under reduced pressure. The mixture was diluted with water and acetonitrile, and was freezer-dried to give 3,9-bis-[2-(pyrrolidin-2-yl)-3H-imidazol-4-yl]-6-methyl-6,7-dihydro-5H-dibenzo[c,e]azepine as brown powder (25 mg). m/z: 480.1 (M+H)+.

Workup

customthe solvents were evaporated under reduced pressure
additionThe mixture was diluted with water and acetonitrile
customwas freezer-dried

Sources & evidence

ORD record: ord-6264e655809d4e05bec1acbd51ee195b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575118B2

Reaction notes

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