1-(Dimethylamino)pent-1-en-3-one → HCID 57829728, compound

HRID 1855465Notes

Reaction equation

HRID 1855465 reaction equation
[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:9][O:10][C:11]1[CH:12]=[C:13]([NH:23][C:24]([NH2:26])=[NH:25])[CH:14]=[CH:15][C:16]=1[N:17]1[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]1.CN(C)[CH:29]=[CH:30][C:31](=O)[CH2:32][CH3:33]>>[CH2:32]([C:31]1[CH:30]=[CH:29][N:26]=[C:24]([NH:23][C:13]2[CH:14]=[CH:15][C:16]([N:17]3[CH:21]=[C:20]([CH3:22])[N:19]=[CH:18]3)=[C:11]([O:10][CH3:9])[CH:12]=2)[N:25]=1)[CH3:33]

Participants

3

Reactant 2

HCID 217684671-(Dimethylamino)pent-1-en-3-oneHCID 178493228HCID 178493228, compound

Product 1

HCID 57829728HCID 57829728, compound

Procedure

The title compound was prepared from N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (149 mg, 0.4 mmol) and 1-dimethylamino-pent-1-en-3-one using (64 mg, 0.5 mmol) using in analogous manner the procedure described in example 139. Obtained as a white solid (18 mg, 16%). MS ISP (m/e): 310.2 [(M+H)+]. NMR (CDCl3, 300 MHz): δ (ppm)=8.33 (d, 1H), 7.81 (d, 1H), 7.63 (s, 1H), 7.25 (s, 1H), 7.15 (d, 1H), 7.07 (dd, 1H), 6.87 (s, 1H), 6.67 (d, 1H), 3.87 (s, 3H), 2.71 (q, 2H), 2.30 (s, 3H), 1.33 (t, 3H).

Sources & evidence

ORD record
ord-6b3659012c424db48034ef560ac46239
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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