Triethylamine → N-{5-Methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]-3-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-N-(methylsulfonyl)methanesulfonamide

HRID 1517056ノート

反応式

HRID 1517056 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([N:10]2[CH2:15][CH2:14][CH:13]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:12][CH2:11]2)=[O:9])[C:5]([CH3:21])=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.CCN(CC)CC.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>CN(C=O)C.CN(C1C=CN=CC=1)C>[CH3:21][C:5]1[CH:4]=[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:2]([N:1]([S:40]([CH3:39])(=[O:42])=[O:41])[S:40]([CH3:39])(=[O:42])=[O:41])=[N:7][C:6]=1[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([N:16]2[CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:12][CH2:11]1)=[O:9]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44547360[6-Amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

生成物 1

HCID 57441126N-{5-Methyl-6-[(4-pyrrolidin-1-ylpiperidin-1-yl)carbonyl]-3-[3-(trifluoromethyl)phenyl]pyridin-2-yl}-N-(methylsulfonyl)methanesulfonamide収率 44.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A solution of 0.22 g (0.5 mmol) of [6-amino-3-methyl-5-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 7) in 5.0 ml of DMF was treated with 0.43 ml=0.309 g (3.1 mmol) of Et3N and 0.006 g (0.05 mmol) of DMAP. To the stirred solution was added 0.08 ml=0.12 g (1.0 mmol) of methanesulfonyl chloride drop by drop and the reaction mixture was subsequently warmed up to 50° C. After 5 hours, it was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1) to give 0.13 g (44%) of the title compound as yellow solid. MS: 589.1 (MH+).

後処理

  1. additionit was poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (CH2Cl2/MeOH 1:0 to 4:1)

出典と根拠

ORDレコード
ord-4578350c84cf43e183516220bd6d7c5e
出典データセット
uspto-grants-2012_07
特許番号
US08227613B2

反応ノート

読み込み中…