3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine → 2-[2-[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol

HRID 1855532Notes

Reaction equation

HRID 1855532 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH2:36])[CH:27]=[CH:28][C:29]=1[C:30]1[S:34][C:33]([CH3:35])=[N:32][CH:31]=1>>[CH3:22][O:23][C:24]1[CH:25]=[C:26]([NH:36][C:2]2[N:7]=[C:6]([C:8]([OH:11])([CH3:10])[CH3:9])[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[N:3]=2)[CH:27]=[CH:28][C:29]=1[C:30]1[S:34][C:33]([CH3:35])=[N:32][CH:31]=1

Participants

3

Reactant 2

HCID 670959033-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamineHCID 866336402-[2-Chloro-6-(4-trifluoromethyl-phenyl)pyrimidine-4-yl]-propan-2-ol

Product 1

HCID 441927002-[2-[3-Methoxy-4-(2-methyl-thiazol-5-yl)-phenylamino]-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-olYield 24%

Procedure

Using in analogous manner the procedure described in example 1e), 2-[2-chloro-6-(4-trifluoromethyl-phenyl)-pyrimidin-4-yl]-propan-2-ol (95 mg, 0.3 mmol) was reacted with 3-methoxy-4-(2-methyl-thiazol-5-yl)-phenylamine (66 mg, 0.3 mmol) to give the title compound as light yellow solid (36 mg, 24%). MS ISP (m/e): 501.1 [(M+H)+]. 1H NMR (CDCl3, 300 MHz): δ (ppm)=8.21 (d, 2H), 7.98 (s, 1H), 7.77 (m, 3H), 7.54 (d, 1H), 7.34 (2 s, 2×1H), 7.10 (dd, 1H), 3.98 (s, 3H), 3.87 (s, 1H), 2.73 (s, 3H), 1.62 (s, 6H).

Sources & evidence

ORD record
ord-494ae855082c4afdaa12bb2581058eee
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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