Hydrochloric Acid → (R)-5-(2-(2-(2-aminoethylamino)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid hydrochloride

HRID 1426923Notes

Reaction equation

HRID 1426923 reaction equation
C(OC([NH:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]2[CH:28]=[CH:27][N:26]3[N:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[C:25]3[N:24]=2)=[CH:16][C:15]([F:35])=[CH:14][N:13]=1)=O)(C)(C)C.[ClH:36]>C(O)(C(F)(F)F)=O>[ClH:36].[NH2:8][CH2:9][CH2:10][NH:11][C:12]1[C:17]([C@H:18]2[CH2:22][CH2:21][CH2:20][N:19]2[C:23]2[CH:28]=[CH:27][N:26]3[N:29]=[CH:30][C:31]([C:32]([OH:34])=[O:33])=[C:25]3[N:24]=2)=[CH:16][C:15]([F:35])=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86691722(R)-5-(2-(2-(2-(tert-butoxycarbonylamino)ethylamino)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

Product 1

HCID 86691723(R)-5-(2-(2-(2-aminoethylamino)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-5-(2-(2-(2-(tert-butoxycarbonylamino)ethylamino)-5-fluoropyridin-3-yl)pyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (31 mg, 0.064 mmol) in HCl (4 N dioxane, 798 μL) and TFA (50% DCM, 2 mL) was stirred at ambient temperature for 1 hour before it was concentrated and dried under high vacuum to yield to give the desired product as off-white solid, which was used in the next step directly without further purification, assuming quantitative conversion. MS (apci) m/z=386.1 (M+H).

Workup

  1. concentrationwas concentrated
  2. customdried under high vacuum
  3. customto yield

Sources & evidence

ORD record
ord-6080ae3033624eb8a9265e8bca25005a
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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