Triethylamine → 2-(4-fluorophenyl)-5-(4-methoxy-3-((3-(pyrimidin-2-yl)oxetan-3-yl)carbamoyl)phenyl)-N-methyl-6-nitrobenzofuran-3-carboxamide

HRID 1892566Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([C:24]4[CH:25]=[CH:26][C:27]([O:33][CH3:34])=[C:28]([CH:32]=4)[C:29](O)=[O:30])=[CH:17][C:11]=3[C:12]=2[C:13](=[O:16])[NH:14][CH3:15])=[CH:4][CH:3]=1.Cl.[N:36]1[CH:41]=[CH:40][CH:39]=[N:38][C:37]=1[C:42]1([NH2:46])[CH2:45][O:44][CH2:43]1.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[C:18]([C:24]4[CH:25]=[CH:26][C:27]([O:33][CH3:34])=[C:28]([C:29](=[O:30])[NH:46][C:42]5([C:37]6[N:36]=[CH:41][CH:40]=[CH:39][N:38]=6)[CH2:45][O:44][CH2:43]5)[CH:32]=4)=[CH:17][C:11]=3[C:12]=2[C:13]([NH:14][CH3:15])=[O:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-nitrobenzofuran-5-yl)-2-methoxy-benzoic acid (150 mg, 0.323 mmol) and 3-(pyrimidin-2-yl)oxetan-3-amine hydrochloride (77 mg, 0.42 mmol) in DMF at room temperature under a nitrogen atmosphere (7.5 mL) was added triethylamine (0.225 mL, 1.615 mmol). The mixture was cooled to 0° C. and then added with BOP (214 mg, 0.484 mmol) at the same temperature. The reaction mixture was warmed to rt and stirred at rt overnight. The reaction mixture was then diluted with water and stirred for 5 min. The solid obtained was filtered and dried under suction. Yield: 0.180 g (93%).

Workup

temperatureThe reaction mixture was warmed to rt
stirringstirred for 5 min
customThe solid obtained
filtrationwas filtered
customdried under suction

Sources & evidence

ORD record: ord-f95187b6daf04030b2b0b715a68473e2
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08507683B2

Reaction notes

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