Hydrochloric Acid → HCID 86691735, compound

HRID 1426943Notes

Reaction equation

HRID 1426943 reaction equation
Cl.[F:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][CH2:8][CH2:9][NH:10]C(=O)OC(C)(C)C)=[C:5]([C@H:20]2[CH2:24][CH2:23][CH2:22][N:21]2[C:25]2[CH:30]=[CH:29][N:28]3[N:31]=[CH:32][C:33]([CH:34]=[O:35])=[C:27]3[N:26]=2)[CH:4]=1>C(Cl)Cl>[NH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:18]=[CH:19][C:3]([F:2])=[CH:4][C:5]=1[C@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25]1[CH:30]=[CH:29][N:28]2[N:31]=[CH:32][C:33]([CH:34]=[O:35])=[C:27]2[N:26]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691734HCID 86691734, compound

Product 1

HCID 86691735HCID 86691735, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

An HCl (4N dioxane, 80 μl, 0.32 mmol) was added to a DCM (2 mL) solution of (R)-tert-butyl 2-(4-fluoro-2-(1-(3-formylpyrazolo[1,5-a]pyrimidin-5-yl)pyrrolidin-2-yl)phenoxy)ethylcarbamate (198 mg, 0.422 mmol), and the reaction was purged with N2 and stirred at ambient temperature overnight. After removal of solvent, NaOH (5 mL×1N) was introduced and the reaction mixture was extracted with several portions of DCM in a phase separator tube. The combined organic extracts were concentrated to provide (R)-5-(2-(2-(2-aminoethoxy)-5-fluorophenyl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carbaldehyde (155 mg, 99.5% yield), which was used immediately in the next step. MS (apci) m/z=352.3 (M+H−H2O).

Workup

  1. customthe reaction was purged with N2
  2. customAfter removal of solvent, NaOH (5 mL×1N)
  3. additionwas introduced
  4. extractionthe reaction mixture was extracted with several portions of DCM in a phase separator tube
  5. concentrationThe combined organic extracts were concentrated

Sources & evidence

ORD record
ord-fbe273231c184027a32469aaa6d793a4
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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