Cyclopentylamine → HCID 178430680, compound

HRID 589998Notes

Reaction equation

HRID 589998 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][C:5](=[O:8])[C:4]2=[C:9](S(C)(=O)=O)[S:10][C:11]([C:12]3[CH:16]=[CH:15][NH:14][N:13]=3)=[C:3]12.[CH:21]1([NH2:26])[CH2:25][CH2:24][CH2:23][CH2:22]1>CC(N(C)C)=O>[CH:21]1([NH:26][C:9]2[S:10][C:11]([C:12]3[CH:16]=[CH:15][NH:14][N:13]=3)=[C:3]3[CH:2]([CH3:1])[CH2:7][NH:6][C:5](=[O:8])[C:4]=23)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 178430681HCID 178430681, compound

Product 1

HCID 178430680HCID 178430680, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a sealed tube, the 7-methyl-3-(methylsulfonyl)-1-(1H-pyrazol-3-yl)-6,7-dihydrothieno[3,4-c]pyridin-4(5H)-one from Step 6 (30 mg, 0.096 mmol) was added and dissolved in DMA (193 μl), treated with cyclopentylamine (189 μl, 1.927 mmol) and subjected to microwave conditions: 160° C., 8 hrs, normal absorption. The reaction mixture was diluted with CH2Cl2 and washed with water, dried by filtering through a hydrophobic frit and evaporated to give solid residue. This was purified via reverse phase HPLC (5-95% CH3CN/H2O/0.025% TFA) to give afford the title compound: 1H NMR (400 MHz, CDCl3) δ 8.16 (m, 2H), 7.66 (d, J=2.4 Hz, 1H), 6.43 (d/=2.3 Hz, 1H), 3.75 (m, 1H), 3.63 (dd, J=12.5, 4.4 Hz, 1H), 3.35 (m, 1H), 3.27 (d, J=12.4 Hz, 1H), 2.18 (s, 1H), 2.10 (m, 2H), 1.78 (m, 2H), 1.65 (m, 3H), 1.31 (d, J=7.1 Hz, 3H). LRMS (M+H)+=317.2.

Workup

  1. custom160° C., 8 hrs, normal absorption
  2. additionThe reaction mixture was diluted with CH2Cl2
  3. washwashed with water
  4. customdried
  5. filtrationby filtering through a hydrophobic frit
  6. customevaporated
  7. customto give solid residue
  8. customThis was purified via reverse phase HPLC (5-95% CH3CN/H2O/0.025% TFA)
  9. customto give

Sources & evidence

ORD record
ord-ec662439cf7a47278ba5d3e409fe8482
Source dataset
uspto-grants-2016_01
Patent number
US09233977B2

Reaction notes

Loading…