Triethylamine; trifluoroacetic acid → 2,3-dichloro-N-(2-fluoro-4-(3-(pyrimidin-4-yl)pyridin-2-ylamino)phenyl)benzenesulfonamide

HRID 1361697Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[C:13]=2[Cl:19])(=[O:11])=[O:10])=[C:4]([F:20])[CH:3]=1.Cl[C:22]1[C:27]([C:28]2[CH:33]=[CH:32][N:31]=[CH:30][N:29]=2)=[CH:26][CH:25]=[CH:24][N:23]=1.N(CC)(CC)CC.FC(C(O)=O)(F)F>C(Cl)Cl.CO>[Cl:19][C:13]1[C:14]([Cl:18])=[CH:15][CH:16]=[CH:17][C:12]=1[S:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:22]2[C:27]([C:28]3[CH:33]=[CH:32][N:31]=[CH:30][N:29]=3)=[CH:26][CH:25]=[CH:24][N:23]=2)=[CH:3][C:4]=1[F:20])(=[O:11])=[O:10]

Participants

Conditions

Temperature: 100 °C

Procedure

To N-(4-amino-2-fluorophenyl)-2,3-dichlorobenzenesulfonamide (0.150 g, 0.45 mmol) and 4-(2-chloropyridin-3-yl)pyrimidine (0.086 g, 0.45 mmol) was added NEt3.TFA. The mixture was heated at 100° C. CH2Cl2/MeOH was added, producing a yellow precipitate, which was filtered. Trituration with a further portion of CH2Cl2/MeOH, followed by filtration, afforded 2,3-dichloro-N-(2-fluoro-4-(3-(pyrimidin-4-yl)pyridin-2-ylamino)phenyl)benzenesulfonamide as an orange solid. MS m/z=491 [M+H]+. Calc'd for C21H14Cl2FN5O2S: 490.35.

Workup

customproducing a yellow precipitate, which
filtrationwas filtered
filtrationTrituration with a further portion of CH2Cl2/MeOH, followed by filtration

Sources & evidence

ORD record: ord-15717b2cf1064cb9924ca23edfef2ab4
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880000B2

Reaction notes

Loading…