Dimethylamine → HCID 59454941, compound

HRID 1401484Notes

Reaction equation

HRID 1401484 reaction equation
[CH3:1][N:2]1[CH2:30][CH2:29][C:5]2[N:6]([CH2:14][C:15]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:16][C:17]([O:19]CC)=[O:18])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.CNC>O>[CH3:1][N:2]1[CH2:30][CH2:29][C:5]2[N:6](/[CH:14]=[C:15](/[C:22]3[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=3)\[CH2:16][C:17]([OH:19])=[O:18])[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 66611719HCID 66611719, compound

Product 1

HCID 59454941HCID 59454941, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of ethyl 4-(2,8-dimethyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)-3-(4-fluorophenyl)but-2-enoate (50 mg, 0.123 mmol; prepared according to General Method 5) and 40% aqueous N,N-dimethylamine (1 mL) was heated overnight at 100° C. The reaction mixture was cooled to RT, diluted with water (5 mL) and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated to obtain the crude product, which was triturated with ether to obtain a pale yellow solid. 1H NMR (CD3OD, freebase) δ (ppm): 7.65 (m, 2H), 7.30 (d, 1H), 7.20 (m, 3H), 7.05 (d, 1H), 6.90 (d, 1H), 4.35 (m, 2H), 3.50 (m, 2H), 3.20 (m, 4H), 3.0 (s, 3H), 2.40 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-25224b0b024d4cdf9d3872531e93a25e
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

Loading…