Piperidine → HCID 11705955、化合物

HRID 20569ノート

反応式

HRID 20569 の反応式
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([C:27]([NH:29][C:30]2[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=2)=[O:28])[CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:14]([OH:16])=O.CN(C(ON1N=N[C:51]2[CH:52]=[CH:53][CH:54]=[N:55][C:50]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C=O)C.O>[F:10][C:11]1[CH:12]=[C:13]([C:14]([N:55]2[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]2)=[O:16])[CH:17]=[CH:18][C:19]=1[O:20][C:21]1[CH:26]=[C:25]([CH:24]=[C:23]([O:36][C@@H:37]([CH3:40])[CH2:38][OH:39])[CH:22]=1)[C:27]([NH:29][C:30]1[CH:34]=[CH:33][N:32]([CH3:35])[N:31]=1)=[O:28]

参加物

7

反応物 4

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 593469353-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid

生成物 1

HCID 11705955HCID 11705955、化合物収率 47.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (0.36 mL, 1.95 mmol) was added to a suspension of 3-fluoro-4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(1-methyl-1H-pyrazol-3-yl)amino]carbonyl}phenoxy)benzoic acid (209 mg, 0.49 mmol), HATU (390 mg, 1.02 mmol) and piperidine (0.19 mL, 1.95 mmol) in DMF (3 mL), and the mixture stirred at ambient temperature for 24 hours. Water (30 mL) was added and the mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with a gradient of 0-20% methanol in ethyl acetate, to give the desired compound (116 mg).

後処理

  1. extractionthe mixture extracted with diethyl ether/ethyl acetate 4:1 (3×20 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas chromatographed on silica
  6. washeluting with a gradient of 0-20% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-d5344cbb75354419b82a61858da94bef
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

反応ノート

読み込み中…