2-Chlorobenzoxazole → N-(3-methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzo[d]oxazol-2-amine

HRID 252637Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([NH2:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)=[CH:13][CH:12]=[CH:11][N:10]=1.Cl[C:23]1[O:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1>C1(C)C=CC=CC=1.CS(C)=O>[CH3:1][C:2]1[CH:3]=[C:4]([NH:21][C:23]2[O:24][C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][N:16]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To 3-methyl-4-(3-(pyrimidin-4-yl)pyridin-2-yloxy)benzenamine (30 mg, 0.11 mmol) in toluene (2.0 mL) was added 2-chlorobenzo[d]oxazole (0.014 mL, 0.12 mmol). The resulting mixture was heated to 100° C. for 47 h. The mixture was diluted with DMSO and purified by Gilson reverse-phase HPLC. The product-containing fractions were combined, diluted with methylene chloride, and extracted with saturated sodium carbonate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to yield the title compound as a tan solid. MS m/z=396 [M+H]+. Calc'd for C23H17N6O2: 395.42.

Workup

custompurified by Gilson reverse-phase HPLC
additiondiluted with methylene chloride
extractionextracted with saturated sodium carbonate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-90cc0ad81bc64488b8e68069c786e29f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868177B2

Reaction notes

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