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

HRID 1046967Notes

Reaction equation

HRID 1046967 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:30]=[CH:29][C:28]([C:31]3([NH:35]C(=O)OC(C)(C)C)[CH2:34][CH2:33][CH2:32]3)=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:43]>ClCCl.O1CCOCC1.CCOCC>[ClH:43].[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]([C:31]3([NH2:35])[CH2:34][CH2:33][CH2:32]3)=[CH:29][CH:30]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 69087617HCID 69087617, compound

Product 1

HCID 675036931-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutyl)carbamate (0.55 g) in dichloromethane (50 mL) was added 4.0 M HCl in dioxane (5 mL). The reaction was stirred at room temperature for 6 hours and then diluted with ether (50 mL). The product was removed by filtration under reduced pressure and dried to give 1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)cyclobutanamine hydrochloride as a pale yellow solid (0.52 g, 88% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.80 (bs, 3H), 8.68 (s, 1H), 8.12 (dd, JA=4.8 Hz, JB=1.6 Hz, 1H), 7.98-7.95 (m, 1H), 7.57-7.48 (m, 4H), 7.43-7.27 (m, 7H), 7.15 (t, J=7.2 Hz, 1H), 6.91-6.88 (m, 1H), 6.79-6.74 (m, 1H), 2.56 (t, J=8 Hz, 4H), 2.24-2.16 (m, 1H), 1.85-1.77 (m, 1H); LCMS: 456 [M+H]. Calc. for C30H25N5.3.07HCl.0.14 dioxane.0.28 diethylether: C, 63.36; H, 5.37; N, 11.66. Found C, 63.36; H, 5.50; N, 11.67.

Workup

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

Sources & evidence

ORD record
ord-7b67a07ce8d74dd0ad935dd51e7d14aa
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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