Methanesulfonamide → 5-chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide hydrochloride salt

HRID 2048033Notes

Reaction equation

HRID 2048033 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[N:15][C:16]([CH:24]3[CH2:26][CH2:25]3)=[C:17]([O:19][C:20]([F:23])([F:22])[CH3:21])[CH:18]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7](O)=[O:8].[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>ClCCl>[ClH:1].[Cl:1][C:2]1[C:3]([O:12][C:13]2[CH:14]=[N:15][C:16]([CH:24]3[CH2:26][CH2:25]3)=[C:17]([O:19][C:20]([F:23])([F:22])[CH3:21])[CH:18]=2)=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([NH:31][S:28]([CH3:27])(=[O:30])=[O:29])=[O:8]

Participants

6

Reactant 4

HCID 72879MethanesulfonamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580424975-Chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluorobenzoic acid

Product 1

HCID 671226175-chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluoro-N-(methylsulfonyl)benzamide hydrochloride salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dichloromethane (10 mL) solution of 5-chloro-4-(6-cyclopropyl-5-(1,1-difluoroethoxy)pyridin-3-yloxy)-2-fluorobenzoic acid (Preparation 271, 220 mg, 0.57 mmol) was added methanesulfonamide (64 mg, 0.68 mmol), HATU (259 mg, 0.68 mmol), and DIPEA (0.35 mL, 1.99 mmol). The reaction was left to stir at room temperature for 2 hours. The reaction was washed with a 2M aqueous solution of HCl (50 mL) and extracted into DCM (3×50 mL). The combined organics were dried over MgSO4, filtered and the solvent removed to leave an off white solid. The solid was triturated in a minimum of methanol, filtered and dried in air, to leave the title compound as a white solid as the HCl salt. (131 mg, 50%).

Workup

  1. waitThe reaction was left
  2. washThe reaction was washed with a 2M aqueous solution of HCl (50 mL)
  3. extractionextracted into DCM (3×50 mL)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto leave an off white solid
  8. customThe solid was triturated in a minimum of methanol
  9. filtrationfiltered
  10. customdried in air

Sources & evidence

ORD record
ord-26739f75fcbc474dae78ef12152d2efd
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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