Diisopropylethylamine → HCID 117761045、化合物

HRID 523262ノート

反応式

HRID 523262 の反応式
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH2:15][C:16](O)=[O:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:16](=[O:17])[CH2:15][C:11]2[S:10][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][CH:8]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 212206632-Thiazoleacetic acid

生成物 1

HCID 117761045HCID 117761045、化合物収率 42.3%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-bromo-2-methylaniline (0.764 mL, 6.20 mmol), 1,3-thiazol-2-ylacetic acid (0.74 g, 5.17 mmol) and DIEA (1.63 mL, 9.30 mmol) in DMF (15 mL) was treated with HATU (2.36 g, 6.20 mmol). After stirring overnight, the mixture was diluted with EtOAc, washed twice with 10% aqueous LiCl followed by brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes, to give N-(3-bromo-2-methylphenyl)-2-(thiazol-2-yl)acetamide as a white solid (0.681 g, 42% yield). 1H NMR (400 MHz, chloroform-d) δ 9.84-9.65 (m, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.84 (d, J=3.3 Hz, 1H), 7.42-7.35 (m, 2H), 7.07 (t, J=8.0 Hz, 1H), 4.18 (s, 2H), 2.38 (s, 3H).

後処理

  1. washwashed twice with 10% aqueous LiCl
  2. extractionthe combined aqueous layers were extracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc-hexanes

出典と根拠

ORDレコード
ord-797cbe1dd4a54a20937e61a4826ab618
出典データセット
uspto-grants-2016_05
特許番号
US09334290B2

反応ノート

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