Diisopropylethylamine → HCID 70169347, compound

HRID 1426939Notes

Reaction equation

HRID 1426939 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:18]1[CH:23]=[CH:22][N:21]2[N:24]=[CH:25][C:26]([C:27]([O:29]CC)=O)=[C:20]2[N:19]=1.CCN(C(C)C)C(C)C>CCO>[F:12][C:9]1[CH:8]=[C:7]2[C:6](=[CH:11][CH:10]=1)[O:5][CH2:4][CH2:3][CH2:2][NH:1][C:27](=[O:29])[C:26]1=[C:20]3[N:19]=[C:18]([CH:23]=[CH:22][N:21]3[N:24]=[CH:25]1)[N:14]1[C@@H:13]2[CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 86691732(R)-ethyl 5-(2-(2-(3-aminopropoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 70169347HCID 70169347, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

(R)-ethyl 5-(2-(2-(3-aminoprop oxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (10 mg, 0.023 mmol) and DIEA (8.1 μL, 0.047 mmol) were combined in dry EtOH (0.1 mL) in a sealed vessel and heated at 200° C. overnight. The reaction was concentrated and purified by reverse-phase column chromatography (0-70% acetonitrile/H2O) to afford the title compound (4.5 mg, 50% yield). MS (apci) m/z=382.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated
  2. custompurified by reverse-phase column chromatography (0-70% acetonitrile/H2O)

Sources & evidence

ORD record
ord-a31a65cebbb74d4497050f9ed00b36cc
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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