Diisopropylethylamine → 4-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-5-trifluoromethyl-indol-1-yl)-amide

HRID 2382091ノート

反応式

HRID 2382091 の反応式
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=2)[N:4]([NH2:15])[CH:3]=1.[CH3:16][C:17]1[C:22]([C:23](O)=[O:24])=[CH:21][N:20]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[N:18]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([F:14])([F:12])[F:13])[CH:9]=2)[N:4]([NH:15][C:23]([C:22]2[C:17]([CH3:16])=[N:18][C:19]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=3)=[N:20][CH:21]=2)=[O:24])[CH:3]=1

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 617020254-Methyl-2-(pyridin-2-yl)pyrimidine-5-carboxylic acidHCID 685567693-Methyl-5-trifluoromethyl-indol-1-ylamine

生成物 1

HCID 592000684-Methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-5-trifluoromethyl-indol-1-yl)-amide収率 28.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 3-methyl-5-trifluoromethyl-indol-1-ylamine (223 mg, 1.04 mmol), 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (224 g, 1.04 mmol), HATU (475 mg, 1.25 mmol), DIPEA (404 mg 3.13 mmol) is stirred in DMF at 150° C. for 1 h. The reaction is quenched with water, extracted with extracted with EtOAc. The organic layer is dried (Na2SO4), filtered and concentrated. The residue is chromatographed through silica gel eluting with 10% MeOH in DCM to afford 4-methyl-2-pyridin-2-yl-pyrimidine-5-carboxylic acid (3-methyl-5-trifluoromethyl-indol-1-yl)-amide (122 mg, 28%). MS: 412 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.22 (s, 1H), 8.79 (d, 1H), 8.66 (d, 1H), 8.06 (t, 1H), 7.91 (s, 1H), 7.60 (dd, 1H), 7.51 (s, 2H), 7.29 (s, 3H), 2.88 (s, 3H), 2.40 (s, 3H).

後処理

  1. customThe reaction is quenched with water
  2. extractionextracted
  3. extractionwith extracted with EtOAc
  4. dry with materialThe organic layer is dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is chromatographed through silica gel eluting with 10% MeOH in DCM

出典と根拠

ORDレコード
ord-652241b57ee24167968a3d5c05c2e887
出典データセット
uspto-grants-2012_09
特許番号
US08258130B2

反応ノート

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