Dimethylamine → HCID 11642120, compound

HRID 386195Notes

Reaction equation

HRID 386195 reaction equation
[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH2:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34](=[O:37])[CH2:35]Cl)[CH2:30][CH2:29]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1.[CH3:38][NH:39][CH3:40]>C1COCC1>[NH2:1][C:2]1[C:3]2[N:4]([C:8]([CH2:27][CH:28]3[CH2:33][CH2:32][N:31]([C:34](=[O:37])[CH2:35][N:39]([CH3:40])[CH3:38])[CH2:30][CH2:29]3)=[N:9][C:10]=2[C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18]3)=[CH:13][CH:12]=2)[CH:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 11598700HCID 11598700, compound

Product 1

HCID 11642120HCID 11642120, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1-{4-[8-Amino-1-(2-phenyl-quinolin-7-yl)-imidazo[1,5-a]pyrazin-3-ylmethyl]-piperidin-1-yl}-2-chloro-ethanone (77.00 mg, 0.15 mmol) was transferred to a pressure reaction vessel and dissolved in 3.15 mL of 2M dimethylamine solution in THF. The reaction was heated at 80° C. overnight. The crude product was then condensed and purified by a 5 g Jones silica gel (dry loaded with silica gel; eluted with 100% CH2Cl2→2% (7N NH3) in MeOH/CH2Cl2→5% (7N NH3) in MeOH/CH2Cl2) and afforded the desired product; 1H NMR (400 MHz, CHLOROFORM-d) δ 8.41 (1 H, d, J=0.80), 8.28 (1 H, d, J=8.23), 8.19 (2 H, dd, J=2.04, J=1.55), 7.93 (3 H, m), 7.53 (3 H, dd, J=1.70, J=1.70), 7.53 (3 H, m), 7.23 (1 H, d, J=5.08), 7.15 (1 H, d, 5.06), 5.52 (2 H, m), 4.63 (1 H, d, J=14.08), 4.04 (1 H, d, J=11.88), 2.43 (2 H, q), 2.97 (4 H, d, J=6.08), 2.60 (1 H, t), 2.43 (6 H, s), 2.29 (1 H, m), 1.86 (2 H, d, J=12.96), 1.30 (2 H, m); MS (ES+): m/z 520.11 (5) [MH+]; HPLC: tR=1.73 min (OpenLynx, polar—5 min).

Workup

  1. customcondensed
  2. custompurified by a 5 g Jones silica gel (dry loaded with silica gel; eluted with 100% CH2Cl2→2% (7N NH3) in MeOH/CH2Cl2→5% (7N NH3) in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-f308fd0b10dd45aa8e2e415b78b74c59
Source dataset
uspto-grants-2013_02
Patent number
US08367826B2

Reaction notes

Loading…