Trifluoromethanesulfonic acid → 4-(2-Aminoethylamino)-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxamide trifluoromethanesulfonate

HRID 333091Notes

Reaction equation

HRID 333091 reaction equation
COC1C=CC(C[NH:10][C:11]([C:13]2[C:14]([NH:24][CH2:25][CH2:26][NH:27]C(=O)OC(C)(C)C)=[C:15]3[C:21]([CH3:22])=[N:20][N:19]([CH3:23])[C:16]3=[N:17][CH:18]=2)=[O:12])=CC=1.[F:35][C:36]([F:42])([F:41])[S:37]([OH:40])(=[O:39])=[O:38]>ClCCl.C(OCC)C>[F:35][C:36]([F:42])([F:41])[S:37]([OH:40])(=[O:39])=[O:38].[NH2:27][CH2:26][CH2:25][NH:24][C:14]1[C:13]([C:11]([NH2:10])=[O:12])=[CH:18][N:17]=[C:16]2[N:19]([CH3:23])[N:20]=[C:21]([CH3:22])[C:15]=12

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 86691175tert-Butyl N-[2-[[5-[(4-methoxyphenyl)methylcarbamoyl]-1,3-dimethyl-pyrazolo[3,4-b]pyridin-4-yl]amino]ethyl]carbamate

Product 1

HCID 866911764-(2-Aminoethylamino)-1,3-dimethyl-pyrazolo[3,4-b]pyridine-5-carboxamide trifluoromethanesulfonateYield 117.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-Butyl N-[2-[[5-[(4-methoxyphenyl)methylcarbamoyl]-1,3-dimethyl-pyrazolo[3,4-b]pyridin-4-yl]amino]ethyl]carbamate (43 mg, 0.092 mmol) in dichloromethane (2.0 ml) was added trifluoromethanesulfonic acid (2.0 mL, 22.60 mmol) and the resulting orange-red mixture was stirred at room temperature over night. The reaction mixture was diluted with dichloromethane (40 ml) and diethylether (100 ml) subsequently upon which a white precipitate was formed. The mixture was stirred for 15 minutes after which the white solids were filtered off, washed with diethylether and dried in a stream of air. 43 mg of an off-white solid was obtained and used directly in the next step. MS (ESI) m/z=249.2.

Workup

  1. customwas formed
  2. stirringThe mixture was stirred for 15 minutes after which the white solids
  3. filtrationwere filtered off
  4. washwashed with diethylether
  5. customdried in a stream of air

Sources & evidence

ORD record
ord-8158c3ab2a274833937d94adb4bf4452
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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