Dimethylformamide dimethyl acetal → HCID 58204492, compound

HRID 886188Notes

Reaction equation

HRID 886188 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][N:7]2[CH:21]=1)(=O)[NH2:2].COC(OC)[N:25]([CH3:27])C.Cl.[F:31][C:32]([F:37])([F:36])[CH2:33][NH:34]N>C(O)(=O)C>[F:31][C:32]([F:37])([F:36])[CH2:33][N:34]1[C:1]([C:4]2[N:5]=[C:6]3[C:12]4[CH:13]=[CH:14][C:15]([C:17]([O:19][CH3:20])=[O:18])=[CH:16][C:11]=4[O:10][CH2:9][CH2:8][N:7]3[CH:21]=2)=[N:2][CH:27]=[N:25]1

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 21934076(2,2,2-Trifluoroethyl)hydrazinehydrochlorideHCID 67050624HCID 67050624, compound

Product 1

HCID 58204492HCID 58204492, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Alternatively, and following the procedure for 184, methyl 2-carbamoyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-9-carboxylate was reacted with 1,1-dimethoxy-N,N-dimethylmethanamine, followed by treatment of trifluoroethylhydrazine hydrochloride in acetic acid to provide 185 (65% yield). 1H NMR (400 MHz, DMSO) δ 8.51 (d, J=8.4, 1H), 8.15 (s, 1H), 8.10 (s, 1H), 7.71 (dd, J=8.4, 1.7, 1H), 7.58 (d, J=1.6, 1H), 5.89 (q, J=8.8, 2H), 4.65-4.45 (m, 5H), 3.87 (s, 3H), 3.58-3.37 (m, 7H)

Sources & evidence

ORD record
ord-d3e8ad0d620f47b9b0b08dd1ad21c966
Source dataset
uspto-grants-2012_08
Patent number
US08242104B2

Reaction notes

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