Dimethylformamide diethylacetal → HCID 57829780, compound
Reaction equation
O=[C:2](CCC)C(OCC)=O.CN(C)[CH:13]=[C:14]([CH2:22]CC)[C:15](=O)[C:16](OCC)=O.[N+]([O-])(O)=O.[N+]([O-])(O)=O.[CH3:34][O:35][C:36]1[CH:37]=[C:38]([NH:48][C:49]([NH2:51])=[NH:50])[CH:39]=[CH:40][C:41]=1[N:42]1[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]1.C(C1C(C(OCC)=O)=NC(NC2C=CC(N3C=C(C)N=C3)=C(OC)C=2)=NC=1)C.C(OC([O:87][CH2:88][CH3:89])N(C)C)C>>[CH2:15]([C:14]1[C:13]([C:88]([OH:87])([CH3:89])[CH3:2])=[N:50][C:49]([NH:48][C:38]2[CH:39]=[CH:40][C:41]([N:42]3[CH:46]=[C:45]([CH3:47])[N:44]=[CH:43]3)=[C:36]([O:35][CH3:34])[CH:37]=2)=[N:51][CH:22]=1)[CH3:16]Participants
Procedure
A solution of ethyl 2-oxo-pentanoate (144 mg, 1.0 mmol) in N,N-dimethylformamide diethyl acetal (0.68 mL) was heated to 100° C. for 2 h. The mixture was evaporated under reduced pressure and the remaining crude ethyl 3-[1-dimethylamino-methylidene]-2-oxo-hexanoate was reacted with N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]guanidine dinitrate (298 mg, 0.80 mmol) in analogous manner as described in example 139. The resulting ethyl 5-ethyl-2-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamino]-pyrimidine-4-carboxylate was subjected in analogous manner to the procedure described in example 165 to give the title compound as a light yellow solid (12 mg, 3%). MS ISP (m/e): 368.2 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.31 (s, 1H), 7.63 (s, 1H), 7.53 (d, 1H), 7.23 (s, 1H), 7.18 (d, 1H), 7.04 (dd, 1H), 6.87 (s, 1H), 5.44 (br s, 1H), 3.87 (s, 3H), 2.73 (q, 2H), 2.30 (s, 3H), 1.60 (s, 6H), 1.30 (t, 3H).
Workup
- customThe mixture was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1422367a18064c50bac4c79507ae8481
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962834B2
Reaction notes
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