Triethylamine → Methyl 6-chloro-4'-(dimethylamino)-4-(2-(3-methylisoxazol-5-yl)acetamido)-[1,1'-biphenyl]-3-carboxylate

HRID 2174559노트

반응식

HRID 2174559 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([C:9]2[CH:14]=[CH:13][C:12]([N:15]([CH3:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([O:20][CH3:21])=[O:19].[CH3:22][C:23]1[CH:27]=[C:26]([CH2:28][C:29](O)=[O:30])[O:25][N:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[Cl:8][C:6]1[C:5]([C:9]2[CH:10]=[CH:11][C:12]([N:15]([CH3:16])[CH3:17])=[CH:13][CH:14]=2)=[CH:4][C:3]([C:18]([O:20][CH3:21])=[O:19])=[C:2]([NH:1][C:29](=[O:30])[CH2:28][C:26]2[O:25][N:24]=[C:23]([CH3:22])[CH:27]=2)[CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 41955322-(3-Methyl-1,2-oxazol-5-yl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68352236HCID 68352236, 화합물2회

생성물 1

HCID 68352394Methyl 6-chloro-4'-(dimethylamino)-4-(2-(3-methylisoxazol-5-yl)acetamido)-[1,1'-biphenyl]-3-carboxylate수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of methyl 4-amino-6-chloro-4′-(dimethylamino)-[1,1′-biphenyl]-3-carboxylate (Intermediate 47) (10.8 g, 35.4 mmol) in dichloromethane (525 mL) was added 2-(3-methylisoxazol-5-yl)acetic acid (Aldrich, 5 g, 35.4 mmol), HATU (17.52 g, 46.1 mmol) and triethylamine (11.85 mL, 85 mmol) and the reaction mixture was stirred at room temperature for 72 h. The mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated with hot methanol, filtered and dried to give the title compound methyl 6-chloro-4′-(dimethylamino)-4-(2-(3-methylisoxazol-5-yl)acetamido)-[1,1′-biphenyl]-3-carboxylate (13.91 g, 32.5 mmol, 92% yield) as a beige solid. LCMS: (M+H)+=428; Rt=3.86 min.

후처리

  1. washThe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hot methanol
  6. filtrationfiltered
  7. customdried

출처 및 근거

ORD 기록
ord-765268cfd3914340b80d1f390e7b3a0a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09061998B2

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