Trifluoroacetic acid → 4-{4-[2-(3-Chloro-phenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2h-pyridine-1-sulfonic acid amide

HRID 76043Notes

Reaction equation

HRID 76043 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH2:23][CH2:24][NH:25][CH2:26][CH:27]=4)=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1.C([NH:35][S:36](Cl)(=[O:38])=[O:37])(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O>>[Cl:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]2[O:12][C:13]([C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH2:23][CH2:24][N:25]([S:36]([NH2:35])(=[O:38])=[O:37])[CH2:26][CH:27]=4)=[CH:18][CH:17]=3)=[CH:14][N:15]=2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 131731872(3-chlorophenyl)-{5-[4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-oxazol-2-yl}-amine bis HCl salt

Product 1

HCID 249380244-{4-[2-(3-Chloro-phenylamino)-oxazol-5-yl]-phenyl}-3,6-dihydro-2h-pyridine-1-sulfonic acid amide

Procedure

The title compound is prepared from (3-chlorophenyl)-{5-[4-(1,2,3,6-tetrahydro-pyridin-4-yl)-phenyl]-oxazol-2-yl}-amine bis HCl salt in analogous fashion using N-Boc chlorosulfonamide followed by TFA-mediated deprotection: 1H NMR (400 MHz, DMSO-d6) δ 2.55 (br. s., 2H) 3.15 (t, J=5.56 Hz, 2H) 3.65 (d, J=2.78 Hz, 2H) 6.22 (t, J=3.28 Hz, 1H) 6.92 (dd, J=7.83, 1.52 Hz, 1H) 7.26 (t, J=8.08 Hz, 1H) 7.39-7.53 (m, 7H) 7.79 (t, J=2.02 Hz, 1H); (M+H)+431.1.

Sources & evidence

ORD record
ord-a91fe2ff75c14ab382ab41d0fe08791c
Source dataset
uspto-grants-2014_09
Patent number
US08835451B2

Reaction notes

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