Triethylamine → HCID 11364309, compound

HRID 915856Notes

Reaction equation

HRID 915856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:10]=[C:11]3[C:16]([N:17]4[CH2:22][CH:21]5[CH2:23][CH:18]4[CH2:19][NH:20]5)=[N:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[N:10]=[C:11]3[C:16]([N:17]4[CH2:22][CH:21]5[CH2:23][CH:18]4[CH2:19][N:20]5[S:39]([CH3:38])(=[O:41])=[O:40])=[N:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58959479HCID 58959479, compound

Product 1

HCID 11364309HCID 11364309, compoundYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Rac-(S,S)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-(2,5-diazabicyclo[2.2.1]hept-2-yl)-2H-pyrazolo[4,3-d]pyrimidine 4A-1 (63 mg, 0.12 mmol) in dichloromethane (2 ml) was charged with triethylamine (0.1 ml). Methanesulfonyl chloride (0.01 ml, 0.14 mmol) was added via syringe, and the resultant mixture was stirred at 23° C. for 3 days. The reaction mixture was then washed with water (2 ml) and the layers were separated. The organic solution was dried over anhydrous magnesium sulfate and concentrated. Purification of the residue by reverse-phase HPLC afforded Rac-(S, S)-3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-(5-methanesulfonyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2H-pyrazolo[4,3-d]pyrimidine 6A-1 (63 mg, quantitative): MS: 515.0 (M+1)+; 1H NMR (400 MHz, CD3OD) δ 8.3 (s, 0,5H), 8.1 (s, 0.5H), 7.6 (m, 4H), 7.4 (m, 4H), 6.1 (s, 0.5H), 5.2 (s, 0.5H), 4.7 (m, 1H), 4.4 (m, 0.5H), 4.2 (m, 0.5H), 4.0 (m, 1H), 3.8 (m, 1H), 3.5 (m, 3H), 3.0 (s, 3H).

Workup

  1. washThe reaction mixture was then washed with water (2 ml)
  2. customthe layers were separated
  3. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customPurification of the residue by reverse-phase HPLC

Sources & evidence

ORD record
ord-111c17afaf2d4e65a17a859ef635b5f5
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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