Diisopropylethylamine → ((2S,3R)-2-(Hydroxymethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

HRID 61029ノート

反応式

HRID 61029 の反応式
[CH3:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][NH:4][C@@H:3]1[CH2:8][OH:9].CCN(C(C)C)C(C)C.[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([N:29]2[N:33]=[CH:32][CH:31]=[N:30]2)=[C:24]([CH:28]=1)[C:25](O)=[O:26].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CC(N(C)C)=O>[OH:9][CH2:8][C@@H:3]1[C@H:2]([CH3:1])[CH2:7][CH2:6][CH2:5][N:4]1[C:25]([C:24]1[CH:28]=[C:20]([CH3:19])[CH:21]=[CH:22][C:23]=1[N:29]1[N:33]=[CH:32][CH:31]=[N:30]1)=[O:26]

参加物

6

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 21825032((2S,3R)-3-Methylpiperidin-2-yl)methanolHCID 532601655-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid

生成物 1

HCID 117727618((2S,3R)-2-(Hydroxymethyl)-3-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

((2S,3R)-3-Methylpiperidin-2-yl)methanol from the previous step in DMA (0.2M) was added DIPEA (2 equiv.) followed by 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid (1.2 eq) and HATU (1.1 equiv.). The reaction was allowed to stir at rt for 15 h, and was then concentrated in vacuo to remove the DMAC. The crude residue was taken up in EtOAc and washed with 1M HCl, sat aq. NaHCO3, brine, dried (MgSO4), and concentrated. The crude residue was purified by chromatography on silica gel (EtOAc/hexanes) to give the title compound as a brown oil which crystallized (2.6 g). MS (ESI) 315 (M+H).

後処理

  1. concentrationwas then concentrated in vacuo
  2. customto remove the DMAC
  3. washwashed with 1M HCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude residue was purified by chromatography on silica gel (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-afb1ba5122ec4541b41b3d9a8a4ac77b
出典データセット
uspto-grants-2016_09
特許番号
US09440982B2

反応ノート

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