Triethylamine → HCID 18427385, compound

HRID 1168284Notes

Reaction equation

HRID 1168284 reaction equation
[NH2:1][CH2:2][C:3]1[N:11]=[C:10]2[C:6]([N:7]=[CH:8][N:9]2[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)=[C:5]([NH:18][CH2:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:4]=1.C(N(CC)CC)C.[CH3:40][CH:41]([CH3:47])[CH2:42][S:43](Cl)(=[O:45])=[O:44]>ClCCl>[C:21]1([CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:19][NH:18][C:5]2[N:4]=[C:3]([CH2:2][NH:1][S:43]([CH2:42][CH:41]([CH3:47])[CH3:40])(=[O:45])=[O:44])[N:11]=[C:10]3[C:6]=2[N:7]=[CH:8][N:9]3[CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][O:13]2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1822361-Propanesulfonyl chloride, 2-methyl-2×HCID 229486282-(aminomethyl)-N-(2,2-diphenylethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-amine

Product 1

HCID 18427385HCID 18427385, compoundYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-[2-(aminomethyl)-9-tetrahydro-2H-pyran-2-yl-9H-purin-6-yl]-N-(2,2-diphenylethyl)amine (3.70 g, 8.63 mmol) (Preparation 6) and triethylamine (2.20 g, 21.78 mmol) in dry dichloromethane (20 ml) was treated with 2-methyl-1-propanesulphonyl chloride (1.48 g, 9.46 mmol) and the mixture was stirred at room temperature for 18 hours. TLC indicated that some starting material still remained and so further 2-methyl-1-propanesulphonyl chloride (0.2 g, 1.28 mmol) was added and the mixture was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume) to afford the title compound as a foam (4.4 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hour
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2 by volume)

Sources & evidence

ORD record
ord-054ea54b581d4274ab9720179cb79192
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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