Hydrochloric Acid → (4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)methanamine hydrochloride

HRID 1046963Notes

Reaction equation

HRID 1046963 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]4[N:20]=[CH:21][CH:22]=[CH:23][C:11]=4[N:10]3[C:24]=2[C:25]2[CH:39]=[CH:38][C:28]([CH2:29][NH:30]C(=O)OC(C)(C)C)=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:40]>ClCCl.O1CCOCC1.CCOCC>[ClH:40].[C:1]1([C:7]2[N:8]=[C:9]3[C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=4[NH:13][C:12]4[N:20]=[CH:21][CH:22]=[CH:23][C:11]=4[N:10]3[C:24]=2[C:25]2[CH:26]=[CH:27][C:28]([CH2:29][NH2:30])=[CH:38][CH:39]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 67503559tert-butyl 4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)benzylcarbamate

Product 1

HCID 67503635(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)methanamine hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)benzylcarbamate (0.100 g) in dichloromethane (4 mL) was added 4.0 M HCl in dioxane (1 mL). The reaction was stirred at room temperature for 2 hours and then diluted with ether (20 mL). The product was removed by filtration under reduced pressure and dried to give (4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)methanamine hydrochloride as a bright yellow solid (0.085 g, 83% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.67 (br. s, 1 H), 8.42 (br. s, 3H), 8.13-8.10 (m, 1H), 7.98-7.95 (m, 1H), 7.51-7.42 (m, 4H), 7.39-7.38 (m, 1H), 7.35-7.26 (m, 5H), 7.15 (t, J=7.4 Hz, 1H), 6.93-6.90 (m, 1H), 6.78-6.73 (m, 1H), 4.06 (dd, JA=11.3 Hz, JB=5.9 Hz, 2H); LCMS: 416 [M+H]; Calc. for C27H21N5.3.26 HCl.0.12 dioxane.0.16 diethylether: C, 60.66; H, 4.86; N, 12.58. Found C, 60.66; H, 4.99; N, 12.58.

Workup

  1. customThe product was removed by filtration under reduced pressure
  2. customdried

Sources & evidence

ORD record
ord-14d743593fc0468ab49d695bbfe4e711
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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