Dimethylformamide → HCID 10478148、化合物

HRID 599142

反応式

HRID 599142 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1.[Br:22][CH:23](C)[C:24](Cl)=O.CN([CH:31]=[O:32])C>>[Br:22][CH2:23][CH2:24][C:31]([NH:1][C:2]1[S:3][C:4]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=3)[N:9]=2)=[C:5]([CH3:7])[N:6]=1)=[O:32]

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 979802-Bromopropanoyl chlorideHCID 9857535[4-(2-Amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine

生成物 1

HCID 10478148HCID 10478148、化合物

実験手順

A solution of [4-(2-amino-4-methyl-thiazol-5-yl)-pyrimidin-2-yl]-(4-fluoro-phenyl)-amine (0.3 g, 1.0 mmol) in DMF (2 mL) was cooled on an ice bath and was treated with 2-bromopropionyl chloride (0.17 g, 1.0 mmol). After completion of the addition, the reaction mixture was allowed to stir at room temperature for 18 h. It was poured into ice water and was extracted with CH2Cl2. The organics were combined, washed with brine, dried on MgSO4, and the solvent was evaporated to leave a brown residue. This was purified by SiO2 chromatography (1:1 EtOAc/PE) to afford the title compound as a light yellow solid. Anal. RP-HPLC: tR=17.1 min (0-60% MeCN in 0.1% aq CF3COOH over 20 min, 1 mL/min, purity >93%). 1H-NMR (DMSO-d6) δ: 1.99 (m, 2H, CH2), 2.68 (s, 3H, CH3), 4.65 (m, 2H, CH2), 7.02 (d, 1H, J=5.2 Hz, pyrimidinyl-H), 7.11 (m, 2H, Ph-H), 7.62 (m, 2H, Ph-H), 8.19 (d, 1H, J=5.5 Hz, pyrimidinyl-H).

後処理

  1. additionAfter completion of the addition
  2. extractionwas extracted with CH2Cl2
  3. washwashed with brine
  4. customdried on MgSO4
  5. customthe solvent was evaporated
  6. customto leave a brown residue
  7. customThis was purified by SiO2 chromatography (1:1 EtOAc/PE)

出典と根拠

ORDレコード
ord-0558768922594a01bb7eb03ca018ab45
出典データセット
uspto-grants-2011_03
特許番号
US07897605B2

関連ノート

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