Triethylamine → HCID 67501290, compound

HRID 1631373Notes

Reaction equation

HRID 1631373 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([OH:24])=O)=[C:15]3[N:14]=2)[CH:5]=[N:6][CH:7]=1.[CH:25]1[CH:26]=CC2N(O)N=[N:31][C:29]=2[CH:30]=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.N1CCCC1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C@H:8]2[CH2:12][CH2:11][CH2:10][N:9]2[C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:22]([N:31]4[CH2:26][CH2:25][CH2:30][CH2:29]4)=[O:24])=[C:15]3[N:14]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 31268PyrrolidineHCID 757711-HydroxybenzotriazoleHCID 66847898HCID 66847898, compound

Product 1

HCID 67501290HCID 67501290, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-5-(2-(5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation I, 50 mg, 0.15 mmol) in anhydrous CH2Cl2 (2 mL) was added HOBt (41 mg, 0.31 mmol) followed by EDCI (88 mg, 0.46 mmol). The solution was stirred for 15 minutes, then treated with triethylamine (64 μL, 0.46 mmol) followed by pyrrolidine (38 μL, 0.46 mmol). After stirring at ambient temperature overnight, the reaction mixture was partitioned between saturated NH4Cl (20 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4 and concentrated. The crude material was purified by silica chromatography (2 to 5% MeOH/CH2Cl2) to yield the final product as white solid (38 mg, 65%). LCMS (apci) m/z=381.1 (M+H).

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe reaction mixture was partitioned between saturated NH4Cl (20 mL) and CH2Cl2 (20 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×10 mL)
  4. washThe combined organic phases were washed with brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude material was purified by silica chromatography (2 to 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cd22315cabe3413485a8d81d092203d5
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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