HCID 672599, compound → HCID 25013775, compound

HRID 1987251Notes

Reaction equation

FC1C=C(F)C=CC=1CCC1(C=CC=CC1)C(N)=O.N1SN=C2C(S(NC3C=CC=CC=3C(O)=O)(=O)=O)=CC=CC=12.[N:42]1[S:46][N:45]=[C:44]2[C:47]([S:51]([NH:54][C:55]3[CH:73]=[C:72](C(F)(F)F)[CH:71]=[CH:70][C:56]=3[C:57]([NH:59][C@@H:60]([C:62]3[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=3[F:69])[CH3:61])=[O:58])(=[O:53])=[O:52])=[CH:48][CH:49]=[CH:50][C:43]=12>>[N:42]1[S:46][N:45]=[C:44]2[C:47]([S:51]([NH:54][C:55]3[CH:73]=[CH:72][CH:71]=[CH:70][C:56]=3[C:57]([NH:59][C@@H:60]([C:62]3[CH:67]=[CH:66][C:65]([F:68])=[CH:64][C:63]=3[F:69])[CH3:61])=[O:58])(=[O:53])=[O:52])=[CH:48][CH:49]=[CH:50][C:43]=12

Participants

Reactant 3

HCID 672599HCID 672599, compound

HCID 25014534HCID 25014534, compound

HCID 86616613HCID 86616613, compound

Product 1

HCID 25013775HCID 25013775, compound

Procedure

(R)-2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-N-[1-(2,4-difluorophenyl-ethyl]benzamide. 2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)benzoic acid was coupled with (R) 1-(2,4-difluorophenyl)-ethylamine (see EXAMPLE 39), and the product was purified, as described in EXAMPLE 7 to provide the title compound. MS (ESI): neg. ion m/z 473 [M−H]−. HPLC (reversed-phase): RT=9.64 min). 1H NMR (400 MHz, CDCl3): 11.38 (s, 1H), 8.32 (dd, J=7.1, 1.0 Hz, 1H), 8.16 (dd, J=8.8, 1.0 Hz, 1H), 7.68 (m, 1H), 7.65 (dd, J=8.8, 7.0 Hz, 1H), 7.30 (m, 3H), 6.98 (m, 1H), 6.88 (m, 1H), 6.85 (m, 1H), 6.40 (bd, J=7.6 Hz, 1H), 5.32 (m, 1H), 1.54 (d, J=6.8 Hz, 3H).

Workup

customthe product was purified

Sources & evidence

ORD record: ord-ca623840abd1429397156d70d29e0cb1
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07550492B2

Reaction notes

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