Triethylamine → N-(2-fluorophenyl)-N,8-dimethyl-4H-thieno[3,2-c]chromene-2-carboxamide

HRID 84714

반응식

HRID 84714 반응식
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[O:8][CH2:7][C:6]3[CH:12]=[C:13]([C:15]([OH:17])=O)[S:14][C:5]=3[C:4]=2[CH:3]=1.[CH3:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[F:26].C(N(CC)CC)C>ClCCl.CN(C1C=CN=CC=1)C>[F:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:19]([CH3:18])[C:15]([C:13]1[S:14][C:5]2[C:4]3[CH:3]=[C:2]([CH3:1])[CH:11]=[CH:10][C:9]=3[O:8][CH2:7][C:6]=2[CH:12]=1)=[O:17]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 27590102-Fluoro-N-methylanilineHCID 579005248-methyl-4H-thieno[3,2-c]chromene-2-carboxylic acid

생성물 1

HCID 57900124N-(2-fluorophenyl)-N,8-dimethyl-4H-thieno[3,2-c]chromene-2-carboxamide

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

8-Methyl-4H-thieno[3,2-c]chromene-2-carboxylic acid was converted to the acid chloride as in Example 3, then treated with N-methyl-2-fluoroaniline (1.5 equiv), and triethylamine (5 equiv) in dichloromethane and N,N-dimethyl-4-aminopyridine (0.2 equiv) at 24° C. After about 24 hr, the reaction mixture was diluted with dichloromethane, and the resulting solution was washed with saturated aqueous sodium bicarbonate. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated. Purification by flash column chromatography (5:2/hexanes:ethylacetate) provided 169bp. 1H NMR (500 MHz, CDCl3) δ 7.40 (m, 1 H), 7.31 (m, 1 H), 7.18-7.22 (m, 2 H), 6.80 (s, 1 H), 6.94 (d, J=8.3 Hz, 1 H), 6.77 (d, J=8.2 Hz, 1 H), 6.60 (s, 1 H), 5.00 (s, 2 H), 3.42 (s, 3 H), 2.26 (s, 3 H). LCMS (ESI) m/z: 354.1

후처리

  1. washthe resulting solution was washed with saturated aqueous sodium bicarbonate
  2. dry with materialThe collected organic was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (5:2/hexanes:ethylacetate)
  6. customprovided 169bp

출처 및 근거

ORD 기록
ord-fe53ab6d73964268afe0ef580afafb3a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846762B2

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