Diisopropylethylamine → 3-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methylpyrazin-2-yl)benzamide

HRID 20559

反応式

HRID 20559 の反応式
CC[N:3]([CH:7]([CH3:9])C)[CH:4](C)C.[OH:10][CH2:11][C@H:12]([CH3:40])[O:13][C:14]1[CH:15]=[C:16]([CH:27]=[C:28]([C:30]([NH:32][C:33]2[CH:38]=[N:37][C:36]([CH3:39])=[CH:35][N:34]=2)=[O:31])[CH:29]=1)[O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.N1CCC1>CN(C=O)C.O>[N:3]1([C:22]([C:21]2[CH:20]=[CH:19][C:18]([O:17][C:16]3[CH:27]=[C:28]([CH:29]=[C:14]([O:13][C@@H:12]([CH3:40])[CH2:11][OH:10])[CH:15]=3)[C:30]([NH:32][C:33]3[CH:38]=[N:37][C:36]([CH3:39])=[CH:35][N:34]=3)=[O:31])=[CH:26][CH:25]=2)=[O:23])[CH2:4][CH2:9][CH2:7]1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12308726Azetidine hydrochlorideHCID 593469134-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid

生成物 1

HCID 115399033-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-(5-methylpyrazin-2-yl)benzamide収率 45.7%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (0.4 mL, 2.08 mmol) was added to a suspension of 4-(3-[(1S)-2-hydroxy-1-methylethoxy]-5-{[(5-methylpyrazin-2-yl)amino]carbonyl}phenoxy)benzoic acid (110 mg, 0.26 mmol), HATU (210 mg, 0.55 mmol) and azetidine hydrochloride (49 mg, 0.52 mmol) in DMF (3 mL) and the mixture stirred at RT for 24 hours. Water (30 mL) was added and the mixture extracted with ethyl acetate (3×15 mL). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to a residue which was chromatographed on silica, eluting with 5% methanol in ethyl acetate, to give the desired compound (55 mg).

後処理

  1. extractionthe mixture extracted with ethyl acetate (3×15 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to a residue which
  5. customwas chromatographed on silica
  6. washeluting with 5% methanol in ethyl acetate

出典と根拠

ORDレコード
ord-ce28fb4cf5104a12903315a39263e4f3
出典データセット
uspto-grants-2010_06
特許番号
US07745475B2

関連ノート

読み込み中…