Triethylamine → HCID 178494202, compound

HRID 1631380Notes

Reaction equation

HRID 1631380 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([OH:26])=O)=[C:17]3[N:16]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:48][C@H:49]1[CH2:54][CH2:53][C@H:52]([OH:55])[CH2:51][CH2:50]1.C(N(CC)CC)C>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]2[CH:20]=[CH:19][N:18]3[N:21]=[CH:22][C:23]([C:24]([NH:48][C@H:49]4[CH2:54][CH2:53][C@H:52]([OH:55])[CH2:51][CH2:50]4)=[O:26])=[C:17]3[N:16]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66847769HCID 66847769, compoundHCID 178511715HCID 178511715, compound

Product 1

HCID 178494202HCID 178494202, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-5-(2-(5-fluoro-2-methoxypyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (Preparation K, 30 mg, 0.084 mmol) in anhydrous CH2Cl2 (2 mL) was added HOBt (34 mg, 0.25 mmol) followed by EDCI (48 mg, 0.25 mmol). The solution was stirred for 30 minutes, then treated with (trans)-4-aminocyclohexanol (29 mg, 0.25 mmol) followed by triethylamine (35 μL, 0.25 mmol). After stirring at ambient temperature for 5 hours, the reaction mixture was diluted with EtOAc, washed with saturated NH4Cl (20 mL), saturated NaHCO3, and brine, then dried (Na2SO4), filtered and concentrated. The crude material was purified by silica chromatography (4% MeOH/CH2Cl2) to yield the final product as white solid (23 mg, 60%). LCMS (apci) m/z=455.1 (M+H).

Workup

  1. stirringAfter stirring at ambient temperature for 5 hours
  2. washwashed with saturated NH4Cl (20 mL), saturated NaHCO3, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by silica chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-c8fe33aa7c0841e8bb70622bdae5650b
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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