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

HRID 2174559ノート

反応式

HRID 2174559 の反応式
[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

参加物

6

反応物 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、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-765268cfd3914340b80d1f390e7b3a0a
出典データセット
uspto-grants-2015_06
特許番号
US09061998B2

反応ノート

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