Diisopropylethylamine → HCID 46916848, compound

HRID 1507808Notes

Reaction equation

HRID 1507808 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](S(C)(=O)=O)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1.C(N(C(C)C)CC)(C)C.[NH2:33][C@H:34]1[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35]1>ClCCl>[NH2:1][C:2]1[N:3]=[C:4]([NH:33][C@H:34]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35]2)[C:5]2[N:10]=[C:9]([CH2:11][CH2:12][C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 509418672-(4-Fluorophenethyl)-7-(methylsulfonyl)thiazolo[5,4-d]pyrimidin-5-amine

Product 1

HCID 46916848HCID 46916848, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-[2-(4-fluorophenyl)ethyl]-7-methanesulfonyl-thiazolo[5,4-d]pyrimidine (150 mg, 0.42 mmol) in dichloromethane (10 ml) was added diisopropylethylamine (3.0 mmol, 492 μL) and tert-butyl 3-(S)-aminopyrrolidine-1-carboxylate (2.1 mmol). The reaction mixture was refluxed for 40 hours whereupon the mixture was extracted with a saturated sodium bicarbonate solution. The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo. The resulting residue was purified by flash chromatography on silica, the mobile phase being a mixture of methanol and dichloromethane (in a ratio gradually ranging from 100% CH2Cl2 to 1% CH3OH in CH2Cl2), yielding the pure title compound (81 mg) which was characterized by its mass spectrum: MS m/z (%): 459 ([M+H]+, 100).

Workup

  1. temperatureThe reaction mixture was refluxed for 40 hours whereupon the mixture
  2. extractionwas extracted with a saturated sodium bicarbonate solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe resulting residue was purified by flash chromatography on silica
  6. additiona mixture of methanol and dichloromethane (in a ratio

Sources & evidence

ORD record
ord-039a492ac8994767bed3609e24d5492e
Source dataset
uspto-grants-2015_12
Patent number
US09221822B2

Reaction notes

Loading…