Aminoacetaldehyde dimethyl acetal → HCID 178495890, compound

HRID 1852421Notes

Reaction equation

HRID 1852421 reaction equation
Cl[C:2]1[C:8]2[CH:9]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=3)[CH:11]=[CH:12][C:7]=2[O:6][CH2:5][CH2:4][N:3]=1.[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26][NH2:27]>>[CH3:23][O:24][CH:25]([O:28][CH3:29])[CH2:26]/[N:27]=[C:2]1\[NH:3][CH2:4][CH2:5][O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=3)=[CH:9][C:8]\1=2

Participants

3

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 71150396HCID 71150396, compound

Product 1

HCID 178495890HCID 178495890, compound

Procedure

A solution of 5-chloro-7-(4-(trifluoromethyl)phenyl)-2,3-dihydrobenzo[f][1,4]oxazepine (11.7 mmol) in 2,2-dimethoxyethanamine (20 mL) was heated at 100° C. for 1 hour. The reaction mixture was concentrated to give (Z)-2,2-dimethoxy-N-(7-(4-(trifluoromethyl)phenyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ylidene)ethanamine as an oil. The crude material was dissolved in toluene (80 mL) and PPTS (6.0 g) was added and the mixture was refluxed for 5 h. The reaction mixture partitioned between ethyl acetate and brine and filtered through celite. The organic layer was dried with sodium sulfate and concentrated before being purified by silica gel chromatography (Rf=0.15 in 2:1 hexanes/ethyl acetate) to give 10-(4-(trifluoromethyl)phenyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine as a white solid (2.3 g, 60% over three steps). C18H13F3N2O×TFA. 331.1 (M+1). 1H NMR (DMSO) δ 8.53 (d, J=2.0 Hz, 1H), 7.99 (d, J=8.0 Hz, 2H), 7.91 (dd, J=8.0, 2.0 Hz, 1H), 7.87 (d, J=8.0 Hz, 2H), 7.77 (d, J=12.0 Hz, 2H), 7.30 (d, J=8.8 Hz, 1H), 4.65 (m, 4H). 19F NMR (DMSO) δ −59.21 (s, 3F).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-dccdcb77b1be4f698b19a667f1524e20
Source dataset
uspto-grants-2015_02
Patent number
US08962610B2

Reaction notes

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