Hydrochloric Acid → HCID 67503648, compound

HRID 1046989Notes

Reaction equation

HRID 1046989 reaction equation
[C:1]1([C:7]2[N:11]3[C:12]4[CH:24]=[CH:23][CH:22]=[N:21][C:13]=4[NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:10]3=[N:9][C:8]=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:11]3[C:12]4[CH:24]=[CH:23][CH:22]=[N:21][C:13]=4[NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:10]3=[N:9][C:8]=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 69087651HCID 69087651, compound

Product 1

HCID 67503648HCID 67503648, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (1-(4-(3-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)phenyl)cyclobutyl)carbamate (0.028 g) in dichloromethane (5 mL) was added 4.0 M HCl in dioxane (0.5 mL). The reaction was stirred at room temperature for 6 hours and then diluted with ether (20 mL). The product was removed by filtration under reduced pressure and dried to give 1-(4-(3-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-2-yl)phenyl)cyclobutanamine hydrochloride as a white solid (0.022 g, 77% based on tris HCl salt). M.p.: 252-258° C.; 1H NMR (DMSO-d6) 400 MHz δ 8.78 (br. s, 3 H), 8.73 (br. s, 1H), 8.11 (dd, JA=4.8 Hz, JB=1.2 Hz, 1H), 7.98 (d, J=7.6 Hz, 1H), 7.56 (d, J=8.4 Hz, 2H), 7.51 (d, J=8.8 Hz, 2H), 7.47-7.38 (m, 4H), 7.32 (d, J=8.4 Hz, 1H), 7.30-7.25 (m, 2H), 7.17 (t, J=7.6 Hz, 1H), 6.95 (d, J=7.6 Hz, 1H), 6.77 (dd, JA=7.6 Hz, JB=4.8 Hz, 1H), 2.60-2.52 (m, 4H), 2.24-2.13 (m, 1H), 1.85-1.72 (m, 1H); LCMS: 456 [M+H]; Calc. for C30H25N5.3.86HCl.0.48 diethylether: C, 60.68; H, 5.37; N, 11.08. Found C, 60.68; H, 5.52; N 11.08.

Workup

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

Sources & evidence

ORD record
ord-bf6fab79301f4a1ea5ea9a91029b9144
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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