Dimethylamine → 1-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid dimethylamide

HRID 244438ノート

反応式

HRID 244438 の反応式
[CH2:1]([N:4]1[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:13])([F:12])[F:11])[CH:6]=[C:5]1[C:31](O)=[O:32])[CH:2]=[CH2:3].[CH2:34]([N:36](CC)[CH2:37]C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CNC>CN(C=O)C.[Cl-].[Na+].O.O>[CH3:34][N:36]([CH3:37])[C:31]([C:5]1[N:4]([CH2:1][CH:2]=[CH2:3])[CH:8]=[C:7]([C:9]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[N:19]=[CH:18]3)([OH:14])[C:10]([F:11])([F:12])[F:13])[CH:6]=1)=[O:32]

参加物

8

反応物 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 2724699PyBOPHCID 249590961-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid

生成物 1

HCID 249590951-Allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid dimethylamide収率 84%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 1-allyl-4-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}-1H-pyrrole-2-carboxylic acid (400 mg, 0.87 mmol, 1 equiv.) in 10 ml of DMF was added 0.22 mL of triethylamine (1.7 mmol, 2 equiv.) and PyBOP (500 mg, 0.96 mmol, 1.1 equiv.) followed by dimethylamine (2 M in THF, 1.3 mL, 2.6 mmol, 3 equiv.). After 18 hours, the mixture was diluted with 50 mL of brine and 50 mL of water and extracted with ethyl ether. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by flash chromatography using EtOAc-hexanes (10-60% gradient) to afford 354 mg (84%) of the title compound as a white solid. MS m/z 487.29 (MH+).

後処理

  1. extractionextracted with ethyl ether
  2. customThe combined organic layers were dried
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

出典と根拠

ORDレコード
ord-7fbca7e5cd7f4f2684dc99d71ce8fa68
出典データセット
uspto-grants-2014_02
特許番号
US08658637B2

反応ノート

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