Triethylamine → HCID 178488856、化合物

HRID 1161306ノート

反応式

HRID 1161306 の反応式
[CH:1]1([CH:7]([N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C:22]2[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:8](O)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[NH2:64][C@H:65]1[CH2:70][CH2:69][C@H:68]([OH:71])[CH2:67][CH2:66]1>C(Cl)Cl>[CH:1]1([CH:7]([N:11]2[C:15]3[CH:16]=[C:17]([F:21])[C:18]([F:20])=[CH:19][C:14]=3[N:13]=[C:12]2[C:22]2[C:23]([O:30][CH3:31])=[N:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[C:8]([NH:64][C@H:65]2[CH2:70][CH2:69][C@H:68]([OH:71])[CH2:67][CH2:66]2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66619285Cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acidHCID 178479278HCID 178479278、化合物

生成物 1

HCID 178488856HCID 178488856、化合物収率 90%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution of cyclohexyl-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetic acid (300 mg, 0.70 mmol, 1.0 equiv) in DCM (5 mL) was added triethylamine (142.1 mg, 194.7 μL, 1.39 mmol, 2.0 equiv) and HATU (341.6 mg, 0.90 mmol, 1.3 equiv) and the mixture stirred at 40° C. After 15 min, trans-4-amino-cyclohexanol hydrochloride (137.04 mg, 0.90 mmol, 1.3 equiv; [CAS RN 50910-54-8]) was added and stirring continued at 50° C. for 2 h. Removal of the solvent mixture under reduced pressure and purification by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate yielded 0.33 g (90%) of the title compound. MS (ES+): 529 (M+H).

後処理

  1. stirringstirring
  2. waitcontinued at 50° C. for 2 h
  3. customRemoval of the solvent mixture
  4. customunder reduced pressure and purification by silica column chromatography
  5. washeluting with a gradient of heptane/ethyl acetate

出典と根拠

ORDレコード
ord-ca889a6058a74080a3f039074755c642
出典データセット
uspto-grants-2010_10
特許番号
US07816540B2

反応ノート

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