Diisopropylethylamine → (E)-N-(4-(4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carbonyl)phenyl)benzo[d]thiazole-4-sulfonamide

HRID 2202405노트

반응식

HRID 2202405 반응식
[F:1][C:2]([F:14])([F:13])[CH2:3]/[CH:4]=[CH:5]/[C:6]1([OH:12])[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.[S:15]1[C:19]2=[CH:20][CH:21]=[CH:22][C:23]([S:24]([NH:27][C:28]3[CH:36]=[CH:35][C:31]([C:32](O)=[O:33])=[CH:30][CH:29]=3)(=[O:26])=[O:25])=[C:18]2[N:17]=[CH:16]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>[OH:12][C:6]1(/[CH:5]=[CH:4]/[CH2:3][C:2]([F:1])([F:13])[F:14])[CH2:7][CH2:8][N:9]([C:32]([C:31]2[CH:30]=[CH:29][C:28]([NH:27][S:24]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]4[S:15][CH:16]=[N:17][C:18]=34)(=[O:26])=[O:25])=[CH:36][CH:35]=2)=[O:33])[CH2:10][CH2:11]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 90447571(E)-4-(4,4,4-trifluorobut-1-enyl)piperidin-4-ol

생성물 1

HCID 78427900(E)-N-(4-(4-hydroxy-4-(4,4,4-trifluorobut-1-enyl)piperidine-1-carbonyl)phenyl)benzo[d]thiazole-4-sulfonamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a round-bottom flask was added with (E)-4-(4,4,4-trifluorobut-1-enyl)piperidin-4-ol (50 mg 0.24 mmol), 4-(benzo[d]thiazole-4-sulfonamido)benzoic acid (80 mg, 0.24 mmol), DIPEA (155 mg, 1.2 mmol), HATU (110 mg, 0.29 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), 8.19 (d, J=8.1 Hz, 1H), 8.10 (d, J=7.5 Hz, 1H), 7.99 (s, 1H), 7.54 (t, J=7.8 Hz, 1H), 7.17-7.24 (m, J=8.3 Hz, 2H), 7.08-7.15 (m, J=8.1 Hz, 2H), 5.78-5.94 (m, 1H), 5.64-5.76 (m, 1H), 4.28-4.47 (m, 1H), 3.51 (s, 1H), 3.32-3.48 (m, 1H), 3.27 (br. s., 1H), 2.84 (dd, J=10.5, 7.0 Hz, 1H), 1.66 (br. s., 4H), 1.46 (d, J=9.7 Hz, 2H). LC-MS: m/z 526.7 (M+H)+

후처리

  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

출처 및 근거

ORD 기록
ord-999a244a40954a16ba5a19cc1fb4cbad
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365545B2

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