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

HRID 2048033노트

반응식

HRID 2048033 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-26739f75fcbc474dae78ef12152d2efd
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08592629B2

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