(E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one → (3-Chloro-4-morpholin-4-yl-phenyl)-[4-(3-isopropyl-2-methyl-3H-imidazol-4-yl)-pyrimidin-2-yl]-amine

HRID 1441331Notes

Reaction equation

HRID 1441331 reaction equation
C(=O)(O)O.[Cl:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]([NH2:21])=[NH:20])[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.CN(C)/[CH:24]=[CH:25]/[C:26]([C:28]1[N:32]([CH:33]([CH3:35])[CH3:34])[C:31]([CH3:36])=[N:30][CH:29]=1)=O>>[Cl:5][C:6]1[CH:7]=[C:8]([NH:18][C:19]2[N:21]=[C:26]([C:28]3[N:32]([CH:33]([CH3:35])[CH3:34])[C:31]([CH3:36])=[N:30][CH:29]=3)[CH:25]=[CH:24][N:20]=2)[CH:9]=[CH:10][C:11]=1[N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1

Participants

3

Reactant 2

HCID 22273494(E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-oneHCID 178512569HCID 178512569, compound

Product 1

HCID 68688719(3-Chloro-4-morpholin-4-yl-phenyl)-[4-(3-isopropyl-2-methyl-3H-imidazol-4-yl)-pyrimidin-2-yl]-amine

Procedure

The title compound was prepared using the procedure described in Example 112, employing N-(3-chloro-4-morpholin-4-yl-phenyl)-guanidine carbonate (Method 17; 500 mg, 1.97 mmol), and (2E)-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (Method 24 of WO 03/076436; 363 mg, 1.64 mmol). Yield: 412 mg, 61% as a white solid. NMR: 1.42 (d, 6H), 2.47 (s, 3H), 2.90 (t, 4H), 3.72 (t, 4H), 5.60 (m, 1H), 7.02 (d, 1H), 7.10 (d, 1H), 7.40 (s, 1H), 7.54 (dd, 1H), 7.78 (d, 1H), 8.37 (d, 1H), 9.43 (s, 1H); m/z 413.

Sources & evidence

ORD record
ord-78bd6612bd494370be23b182e2074511
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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