Dimethylamine → HCID 25142600, compound

HRID 1920754Notes

Reaction equation

HRID 1920754 reaction equation
[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:30]Br)=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:32][NH:33][CH3:34]>>[C:1]1([C@@H:7]([NH:10][C:11]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:23])[N:15]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:30][N:33]([CH3:34])[CH3:32])=[O:12])[CH2:8][CH3:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 674DimethylamineHCID 57733278HCID 57733278, compound

Product 1

HCID 25142600HCID 25142600, compound

Procedure

A mixture of 3-bromomethyl-1-oxo-2-phenyl-1,2-dihydro-isoquinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide (70 mg, 0.147 mmol) and dimethylamine (1 ml of 33% solution in abs. ethanol, excess) was kept at 50° C. for 10 min and then evaporated in vacuo. The residue was dissolved in methanol and passed through SCX cation exchange column (1 g, RSO3H form). Uncharged impurities were eluted with methanol and the product was eluted with 4M NH3 in methanol to give 53 mg of colourless glass-like solid. It was further purified by flash chromatography on SiO2 (5 g, gradient 1,2-dichloroethane—10% ethyl acetate in 1,2-dichloroethane) to give 45 mg of colourless solid. Yield 70%. LC-MS (m/z) 440.1 (MH+); tR=0.88. 1H NMR (250 MHz, DMSO-d6, T=333 K): 0.92 (t, 2H), 1.83 (two overlapping m, 2H), 1.66 (s, 6H), 2.96 and 3.08 (two d of CHAHBN, 2H), 4.96 (q, 1H), 7.19-7.56 (m, 12H), 7.68 (t, 1H), 8.21 (d, 1H), 8.75 (d, 1H).

Workup

  1. customevaporated in vacuo
  2. dissolutionThe residue was dissolved in methanol
  3. washwere eluted with methanol
  4. washthe product was eluted with 4M NH3 in methanol

Sources & evidence

ORD record
ord-f27bb02df8ec40799e00882c5f9a52e3
Source dataset
uspto-grants-2012_05
Patent number
US08173639B2

Reaction notes

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