Diisopropylethylamine → N-(4-(4-(3,3-difluoro-2-methylpropyl)-4-hydroxypiperidine-1-carbonyl)phenyl) benzo[d]thiazole-4-sulfonamide

HRID 2202409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202409
[F:1][CH:2]([F:13])[CH:3]([CH3:12])[CH2:4][C:5]1([OH:11])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[S:14]1[C:18]2=[CH:19][CH:20]=[CH:21][C:22]([S:23]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=3)(=[O:25])=[O:24])=[C:17]2[N:16]=[CH:15]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:13][CH:2]([F:1])[CH:3]([CH3:12])[CH2:4][C:5]1([OH:11])[CH2:6][CH2:7][N:8]([C:31]([C:30]2[CH:29]=[CH:28][C:27]([NH:26][S:23]([C:22]3[CH:21]=[CH:20][CH:19]=[C:18]4[S:14][CH:15]=[N:16][C:17]=34)(=[O:25])=[O:24])=[CH:35][CH:34]=2)=[O:32])[CH2:9][CH2:10]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 904190164-(3,3-Difluoro-2-methylpropyl)piperidin-4-ol

Produkt 1

HCID 78427901N-(4-(4-(3,3-difluoro-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 4-(3,3-difluoro-2-methylpropyl)piperidin-4-ol (110 mg 0.57 mmol), 4-(benzo[d]thiazole-4-sulfonamido)benzoic acid (190 mg, 0.57 mmol), DIPEA (367 mg, 2.8 mmol), HATU (261 mg, 0.69 mmol), and DCM (5 mL). The mixture was stirred at r.t. for 16 hours. After washing with 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), 8.20 (d, J=8.1 Hz, 1H), 8.10 (d, J=7.5 Hz, 1H), 7.94 (s, 1H), 7.55 (t, J=7.9 Hz, 1H), 7.20 (d, J=8.5 Hz, 2H), 7.12 (d, J=8.6 Hz, 2H), 5.90-5.61 (m, 1H), 4.36 (s, 1H), 3.57-3.42 (m, 1H), 3.21 (s, 2H), 2.24 (d, J=7.6 Hz, 1H), 2.05 (s, 1H), 1.86-1.77 (m, 2H), 1.36 (dd, J=14.8, 6.3 Hz, 4H), 1.10 (d, J=7.0 Hz, 3H). LC-MS: m/z 510.5 (M+H)+

Aufarbeitung

  1. washAfter washing with brine
  2. customthe 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-59e9fd50cf8e4c959bb39774919ea815
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365545B2

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