Trifluoroacetic acid → 5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide 2,2,2-trifluoroacetate

HRID 1473430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473430
COC1C=C(OC)C=CC=1C[N:6]([C:31]1[S:32][CH:33]=[CH:34][N:35]=1)[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][C:16]=2[CH:20]2[CH2:24][CH2:23][CH2:22][N:21]2[CH:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[CH:11]=1)(=[O:9])=[O:8].[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43]>C(Cl)Cl>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[O:28]1[CH2:29][CH2:30][CH:25]([N:21]2[CH2:22][CH2:23][CH2:24][CH:20]2[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:17]=2[CH:18]=[CH:19][C:10]([S:7]([NH:6][C:31]2[S:32][CH:33]=[CH:34][N:35]=2)(=[O:8])=[O:9])=[CH:11]3)[CH2:26][CH2:27]1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 86687474N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide

Produkt 1

HCID 866874755-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide 2,2,2-trifluoroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

N-(2,4-dimethoxybenzyl)-5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide (0.038 g, 0.065 mmol) was dissolved in DCM (1 mL) and TFA (0.1 ml, 1.298 mmol) was added. The reaction was stirred for 30 minutes at room temperature. The reaction was concentrated, triturated with diethyl ether, and filtered. The solids were washed with diethyl ether and vacuum dried overnight to afford 5-(1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-2-yl)-N-(thiazol-2-yl)naphthalene-2-sulfonamide 2,2,2-trifluoroacetate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm=12.79 (br. s., 1H), 9.65 (br. s., 1H), 8.55 (br. s., 1H), 8.43 (d, J=9.1 Hz, 1H), 8.27 (d, J=7.2 Hz, 1H), 8.04 (d, J=7.3 Hz, 1H), 7.91 (d, J=8.9 Hz, 1H), 7.82-7.72 (m, 1H), 7.27 (d, J=4.6 Hz, 1H), 6.85 (d, J=4.5 Hz, 1H), 5.61 (d, J=6.1 Hz, 1H), 3.91-3.68 (m, 5H), 3.63-3.45 (m, 3H), 3.13 (t, J=11.3 Hz, 3H), 2.71-2.57 (m, 2H), 2.20 (br. s., 2H), 1.98 (br. s., 1H), 1.84 (d, J=10.5 Hz, 1H), 1.65 (br. s., 2H), 1.51 (br. s., 1H). m/z (ESI) 444.2 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customtriturated with diethyl ether
  3. filtrationfiltered
  4. washThe solids were washed with diethyl ether and vacuum
  5. customdried overnight

Quellen und Nachweise

ORD-Eintrag
ord-7e32538a37074ff2ad45f570b514b911
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012443B2

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