3-(Methoxycarbonyl)benzoic acid → Methyl 3-((2-(6-(3-(trifluoromethyl)benzylamino)pyrimidin-4-yl)-4-chlorophenyl)carbamoyl)benzoate

HRID 1408124Notes

Reaction equation

[F:1][C:2]([F:26])([F:25])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[NH2:21])[N:11]=[CH:10][N:9]=1.CCN=C=NCCCN(C)C.Cl.[CH3:39][O:40][C:41]([C:43]1[CH:44]=[C:45]([CH:49]=[CH:50][CH:51]=1)[C:46](O)=[O:47])=[O:42]>ClCCl.CN(C)C1C=CN=CC=1>[F:26][C:2]([F:25])([F:1])[C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][CH:24]=1)[CH2:6][NH:7][C:8]1[N:9]=[CH:10][N:11]=[C:12]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[NH:21][C:46]([C:45]2[CH:44]=[C:43]([CH:51]=[CH:50][CH:49]=2)[C:41]([O:40][CH3:39])=[O:42])=[O:47])[CH:13]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Into a 100-mL round bottom flask, was placed a solution of N-(3-(trifluoromethyl)benzyl)-6-(2-amino-5-chlorophenyl)pyrimidin-4-amine (500 mg, 1.32 mmol, 1.00 equiv) in dichloromethane (30 mL), EDC.HCl (380 mg, 1.98 mmol, 1.50 equiv), N,N-dimethylpyridin-4-amine (242 mg, 1.98 mmol, 1.50 equiv), and 3-(methoxycarbonyl)benzoic acid (357 mg, 1.98 mmol, 1.50 equiv). The resulting solution was stirred for 2 h at 30° C. in an oil bath. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column and eluted with petroleum ether/ethyl acetate (2:1). The product was obtained as 400 mg (56%) of a yellow solid.

Workup

customInto a 100-mL round bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
washeluted with petroleum ether/ethyl acetate (2:1)

Sources & evidence

ORD record: ord-f3bd02ad2f3649d9b82bf11d055e5293
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916569B2

Reaction notes

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