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

HRID 2202405Notes

Reaction equation

HRID 2202405 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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)+

Workup

  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

Sources & evidence

ORD record
ord-999a244a40954a16ba5a19cc1fb4cbad
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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