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

HRID 2202400노트

반응식

HRID 2202400 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-a19179858ceb4ab9976885919bb4f02e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365545B2

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