Diisopropylethylamine → N-(4-(4-(2-fluoro-2-methylpropyl)-4-hydroxypiperidine-1-carbonyl)phenyl)benzo[d]thiazole-4-sulfonamide

HRID 514864Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 514864
[F:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1([OH:10])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[S:13]1[C:17]2=[CH:18][CH:19]=[CH:20][C:21]([S:22]([NH:25][C:26]3[CH:34]=[CH:33][C:29]([C:30](O)=[O:31])=[CH:28][CH:27]=3)(=[O:24])=[O:23])=[C:16]2[N:15]=[CH:14]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[F:1][C:2]([CH3:12])([CH3:11])[CH2:3][C:4]1([OH:10])[CH2:5][CH2:6][N:7]([C:30]([C:29]2[CH:28]=[CH:27][C:26]([NH:25][S:22]([C:21]3[CH:20]=[CH:19][CH:18]=[C:17]4[S:13][CH:14]=[N:15][C:16]=34)(=[O:24])=[O:23])=[CH:34][CH:33]=2)=[O:31])[CH2:8][CH2:9]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 904189724-(Benzo[d]thiazole-4-sulfonamido)benzoic acidHCID 904190284-(2-Fluoro-2-methylpropyl)piperidin-4-ol

Produkt 1

HCID 78427635N-(4-(4-(2-fluoro-2-methylpropyl)-4-hydroxypiperidine-1-carbonyl)phenyl)benzo[d]thiazole-4-sulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round-bottom flask was added with 4-(2-fluoro-2-methylpropyl) piperidin-4-ol (25 mg 0.143 mmol), 4-(benzo[d]thiazole-4-sulfonamido)benzoic acid (47 mg, 0.143 mmol), DIPEA (110 mg, 0.85 mmol), HATU (54 mg, 0.143 mmol), and DCM (5 mL). The mixture was stirred at r.t. for 16 hours. After washing with satd. NaHCO3, brine, the combined organic layer was dried over anhy. Na2SO4 and concentrated in vacuo. Purification by a standard method gave the desired compound. 1H NMR (CHLOROFORM-d) δ: 9.31 (s, 1H), 8.19 (dd, J=8.1, 0.8 Hz, 1H), 8.10 (dd, J=7.5, 1.1 Hz, 1H), 7.93 (s, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.16-7.23 (m, J=8.3 Hz, 2H), 7.05-7.15 (m, J=8.3 Hz, 2H), 4.19-4.47 (m, 1H), 3.46 (d, J=15.6 Hz, 1H), 3.35 (d, J=15.3 Hz, 2H), 1.89 (s, 3H), 1.84 (s, 3H), 1.49-1.55 (m, 3H), 1.46 (s, 3H). LC-MS: m/z 492.65 (M+H)+

Aufarbeitung

  1. washAfter washing with satd
  2. dry with materialNaHCO3, brine, the combined organic layer was dried over anhy
  3. concentrationNa2SO4 and concentrated in vacuo
  4. customPurification by a standard method

Quellen und Nachweise

ORD-Eintrag
ord-ef932ca4735b41a0a05a30fce628fe51
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108921B2

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