Hydrochloric Acid → HCID 58204361, compound

HRID 1800095Notes

Reaction equation

F[C:2]1[C:7]([C:8]2[N:18]=[CH:17][C:16]3[O:15][CH2:14][CH2:13][N:12]4[CH:19]=[C:20]([C:22]5[N:26]([CH:27]([CH3:29])[CH3:28])[N:25]=[CH:24][N:23]=5)[N:21]=[C:11]4[C:10]=3[CH:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C[O:31]CCOC.Cl>>[CH:27]([N:26]1[C:22]([C:20]2[N:21]=[C:11]3[C:10]4[CH:9]=[C:8]([C:7]5[C:2](=[O:31])[NH:3][CH:4]=[CH:5][CH:6]=5)[N:18]=[CH:17][C:16]=4[O:15][CH2:14][CH2:13][N:12]3[CH:19]=2)=[N:23][CH:24]=[N:25]1)([CH3:29])[CH3:28]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 80711,2-Dimethoxyethane

HCID 67050761HCID 67050761, compound

Product 1

HCID 58204361HCID 58204361, compound

Conditions

Temperature: 80 °C

Procedure

To a solution of 10-(2-fluoropyridin-3-yl)-2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydroimidazo[1,2-d]pyrido[4,3-f][1,4]oxazepine (0.087 g, 0.22 mmol) in 1,2-Dimethoxyethane (3.00 mL, 28.9 mmol) was added 10% aqueous HCl (3 mL). The reaction was allowed to stir and heat at 80° C. overnight. The reaction was allowed to cool to room temperature and concentrated under reduced pressure to give 269, analyzed by rHPLC. MS: (ESI+)=390.2. 1H NMR (500 MHz, DMSO) δ 9.76 (s, 1H), 8.45-8.39 (m, 2H), 8.04 (s, 1H), 7.93 (s, 1H), 7.47 (dd, J=6.1, 2.1 Hz, 1H), 6.37 (t, J=6.7 Hz, 1H), 5.91 (dt, J=13.3, 6.7 Hz, 2H), 5.91 (dt, J=13.3, 6.7 Hz, 1H), 4.61 (dd, J=13.1, 5.5 Hz, 4H), 1.52 (d, J=6.6 Hz, 6H).

Workup

temperatureto cool to room temperature
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-45b1429491ed476685528674c0af6eb2
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08343955B2

Reaction notes

Loading…