Diisopropylethylamine → HCID 117761045, 화합물

HRID 523262노트

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HRID 523262 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 117761045HCID 117761045, 화합물수율 42.3%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-797cbe1dd4a54a20937e61a4826ab618
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334290B2

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