Triethylamine → 2-(trifluoromethyl)-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyrimidine-5-carboxamide

HRID 388388ノート

反応式

HRID 388388 の反応式
[F:1][C:2]([F:13])([F:12])[C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:11])=O)=[CH:5][N:4]=1.C(Cl)(=O)C(Cl)=O.[F:20][C:21]([F:34])([F:33])[C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][C:27]([CH2:31][NH2:32])=[CH:26][CH:25]=2.C(N(CC)CC)C>ClCCl.CN(C=O)C>[F:12][C:2]([F:1])([F:13])[C:3]1[N:4]=[CH:5][C:6]([C:9]([NH:32][CH2:31][C:27]2[CH:28]=[C:29]3[C:24](=[CH:25][CH:26]=2)[NH:23][C:22]([C:21]([F:34])([F:20])[F:33])=[CH:30]3)=[O:11])=[CH:7][N:8]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 105838892-(trifluoromethyl)pyrimidine-5-carboxylic AcidHCID 58126817(2-(Trifluoromethyl)-1h-indol-5-yl)methanamine2 回

生成物 1

HCID 581268182-(trifluoromethyl)-N-[[2-(trifluoromethyl)-1H-indol-5-yl]methyl]pyrimidine-5-carboxamide収率 57.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

2-(Trifluoromethyl)-5-pyrimidinecarboxylic acid (Bio-Farma) (108 mg, 0.560 mmol) was stirred in dichloromethane (10 ml). Oxalyl chloride (0.082 ml, 0.934 mmol) then DMF (1.808 μl, 0.023 mmol) was added. The reaction mixture was then left to stir for 2 h under Argon gas. The reaction mixture was then evaporated to dryness and the resulting residues were then dissolved in dichloromethane (10 ml). A solution of {[2-(trifluoromethyl)-1H-indol-5-yl]methyl}amine (Intermediate 4, 100 mg, 0.467 mmol) in DCM (10 mL) was added then triethylamine (0.130 ml, 0.934 mmol) was added. The reaction mixture was then left to stir at room temperature for 1 h. The reaction mixture was evaporated to dryness. The resulting residues where then purified on the MDAP to give the title compound (105 mg). m/z (ES+) 389 (M+1); 1H NMR (400 MHz, d6-DMSO): δ 12.24 (1H, s), 9.57 (1H, t), 9.43 (2H, s), 7.68 (1H, s), 7.45 (1H, d), 7.32 (1H, dd), 7.00 (1H, s), 4.63 (2H, d).

後処理

  1. waitThe reaction mixture was then left
  2. customThe reaction mixture was then evaporated to dryness
  3. dissolutionthe resulting residues were then dissolved in dichloromethane (10 ml)
  4. waitThe reaction mixture was then left
  5. stirringto stir at room temperature for 1 h
  6. customThe reaction mixture was evaporated to dryness
  7. customThe resulting residues where then purified on the MDAP

出典と根拠

ORDレコード
ord-78f1e5a2728b4c4db7131134bc33e263
出典データセット
uspto-grants-2013_02
特許番号
US08377941B2

反応ノート

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