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

HRID 2079088Notes

Reaction equation

HRID 2079088 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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, 1H), 7.31 (m, 1H), 7.18-7.22 (m, 2H), 6.80 (s, 1H), 6.94 (d, J=8.3 Hz, 1H), 6.77 (d, J=8.2 Hz, 1H), 6.60 (s, 1H), 5.00 (s, 2H), 3.42 (s, 3H), 2.26 (s, 3H). LCMS (ESI) m/z: 354.1

Workup

  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

Sources & evidence

ORD record
ord-76b65f918e904b1ea91b559c59e2f4cc
Source dataset
uspto-grants-2011_04
Patent number
US07928248B2

Reaction notes

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