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

HRID 1046965Notes

Reaction equation

HRID 1046965 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@@H:31]([NH:33]C(=O)OC(C)(C)C)[CH3:32])=[CH:27][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:41]>ClCCl.O1CCOCC1>[ClH:41].[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@@H:31]([NH2:33])[CH3:32])=[CH:29][CH:30]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69087680HCID 69087680, compound

Product 1

HCID 67503859(S)-1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)ethanamine hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution (S)-tert-butyl (1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)ethyl)carbamate (0.251 g) in dichloromethane (20 mL) was added 4.0 M HCl in dioxane (2 mL). The reaction was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and then diluted with ether (20 mL). The product was removed by filtration under reduced pressure and dried to give (S)-1-(4-(2-phenyl-9H-benzo[f]imidazo[1,2-d]pyrido[2,3-b][1,4]diazepin-3-yl)phenyl)ethanamine hydrochloride as a yellow solid (0.215 g, 98% based on tris HCl salt). 1H NMR (DMSO-d6) 400 MHz δ 8.83 (br. s, 1 H), 8.69 (br. s, 3H), 8.16 (dd, JA=4.7 Hz, JB=1.6 Hz, 1H), 8.00 (d, J=7.8 Hz, 1H), 7.56 (d, J=8.6 Hz, 2H), 7.52-7.44 (m, 3H), 7.40-7.30 (m, 3H), 7.28 (d, J=8.2 Hz, 2H), 7.19 (t, J=7.6 Hz, 1H), 6.95-6.91 (m, 1H), 6.82-6.77 (m, 1H), 4.43 (quint., J=6.1 Hz, 1H), 1.52 (d, J=6.7 Hz, 3H); LCMS: 430 [M+H]; Calc. for C28H23N5.3.5HCl.0.05 dioxane.0.35 diethylether: C, 60.52; H, 5.22; N, 11.92. Found C, 60.57; H, 5.67; N, 12.02.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with ether (20 mL)
  3. customThe product was removed by filtration under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-3e17108caecb41d9811be819634db6a0
Source dataset
uspto-grants-2013_10
Patent number
US08569331B2

Reaction notes

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