Diisopropylcarbodiimide → HCID 70817382、化合物

HRID 402467

反応式

HRID 402467 の反応式
[CH3:1][N:2]1[C:6]2=[N:7][C:8]([O:15][CH2:16][C:17]([OH:19])=O)=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:5]2[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:3]1.CC(C)N=C=NC(C)C.C1C=CC2N(O)N=NC=2C=1.[CH3:45][O:46][C:47]1[CH:55]=[CH:54][C:50]([C@@H:51]([NH2:53])[CH3:52])=[CH:49][CH:48]=1>CN(C=O)C>[CH3:45][O:46][C:47]1[CH:55]=[CH:54][C:50]([C@@H:51]([NH:53][C:17](=[O:19])[CH2:16][O:15][C:8]2[N:7]=[C:6]3[N:2]([CH3:1])[N:3]=[C:4]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:5]3=[C:10]([C:11]([F:13])([F:14])[F:12])[CH:9]=2)[CH3:52])=[CH:49][CH:48]=1

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 793467(S)-1-(4-Methoxyphenyl)ethylamineHCID 67209383HCID 67209383、化合物

生成物 1

HCID 70817382HCID 70817382、化合物収率 63.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of (1-Methyl-3-phenyl-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-acetic acid (350 mg, 0.996 mmol), DIC (189 mg, 1.494 mmol) and HOBt (175 mg, 1.295 mmol) in DMF (10 ml) was stirred at rt for 10 min. (S)-(−)-4-methoxy-α-methyl benzyl amine (166 mg, 1.096 mmol) was added to the reaction mixture at rt and stirring was continued for 12 h at rt. After completion of the reaction, the reaction mixture was poured into rapidly stirred ice-cold water to obtain the crude product as a solid. The solid was collected by filtration and dried under vacuum. The product was further purified by flash column chromatography [(eluent: EtOAc/hexane (1:3)] to yield the title compound as a white solid (305 mg, 63%). [1H-NMR (CDCl3, 300 MHz) δ 7.58-7.39 (m, 5H), 7.32-7.21 (m, 2H), 6.99 (s, 1H), 6.85 (d, 2H), 6.51 (d, 1H), 5.31-5.22 (m, 1H), 5.0 (s, 2H), 4.05 (s, 3H), 3.8 (s, 3H), 1.52 (d, 3H); HPLC RtB=5.933 min. (98%); LCMS RtA=1.785, [M+H]+=485.1; Mp=172-174° C.]

後処理

  1. additionwas added to the reaction mixture at rt
  2. customAfter completion of the reaction
  3. additionthe reaction mixture was poured into rapidly stirred ice-cold water
  4. customto obtain the crude product as a solid
  5. filtrationThe solid was collected by filtration
  6. customdried under vacuum
  7. customThe product was further purified by flash column chromatography [(eluent

出典と根拠

ORDレコード
ord-9f08531e86634f7895576b37ce944f5d
出典データセット
uspto-grants-2014_06
特許番号
US08742106B2

関連ノート

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