Diisopropylethylamine → HCID 76284186, compound

HRID 1049051Notes

Reaction equation

HRID 1049051 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16](O)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[NH2:25][CH:26]1[CH2:31][CH2:30][N:29]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:28][CH2:27]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>CN(C=O)C.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:21][CH:22]([CH3:23])[CH3:24])[S:9]([C:12]2[CH:20]=[CH:19][C:15]([C:16]([NH:25][CH:26]3[CH2:31][CH2:30][N:29]([S:32]([CH3:35])(=[O:34])=[O:33])[CH2:28][CH2:27]3)=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:4][CH:3]=1

Participants

7

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 113558261-(Methanesulfonyl)piperidin-4-amineHCID 86721894HCID 86721894, compound

Product 1

HCID 76284186HCID 76284186, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-[(4-fluoro-phenyl)-isobutyl-sulfamoyl]-benzoic acid (100 mg, 0.285 mmol), 4-amino-1-methanesulfonyl piperidine (66 mg, 0.370 mmol) and DIPEA (146 μL, 0.855 mmol) in DMF (2 mL) was treated with HATU (162 mg, 0.428 mmol) and stirred at room temperature for 18 hours. The mixture was diluted with EtOAc, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-50% EtOAc in DCM) and triturating with Et2O gave the title compound (124 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.60 (d, J=7.6 Hz, 1H), 8.00 (d, J=8.3 Hz, 2H), 7.63 (d, J=8.3 Hz, 2H), 7.20 (t, J=8.7 Hz, 2H), 7.11 (dd, J=8.8, 5.0 Hz, 2H), 3.93-3.95 (m, 1H), 3.58 (d, J=11.8 Hz, 2H), 2.88 (s, 5H), 1.93 (s, 1H), 1.90 (s, 2H), 1.58-1.61 (m, 2H), 1.42-1.44 (m, 1H), 0.85 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 511.8 [M+1]+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customPurification by silica gel column chromatography (0-50% EtOAc in DCM)
  5. customtriturating with Et2O

Sources & evidence

ORD record
ord-56967e96604247d38701e5b3b66b51a3
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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