tert-butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1-(ethoxycarbonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)piperidine-1-carboxylate → HCID 25260760, compound

HRID 1093239Notes

Reaction equation

HRID 1093239 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:37])[NH:23][CH:24]4[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26][CH2:25]4)=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:38]([CH:41]4[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:43][CH2:42]4)[N:39]=[CH:40][C:10]=13)[CH2:2]2>C(Cl)Cl.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[N:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:23][CH:24]4[CH2:25][CH2:26][NH:27][CH2:28][CH2:29]4)=[O:37])=[CH:17][CH:16]=3)[N:12]=[C:11]3[N:38]([CH:41]4[CH2:46][CH2:45][N:44]([C:47]([O:49][CH2:50][CH3:51])=[O:48])[CH2:43][CH2:42]4)[N:39]=[CH:40][C:10]=13)[CH2:2]2

Participants

5

Reactant 1

HCID 25262467tert-butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1-(ethoxycarbonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)piperidine-1-carboxylate

Product 1

HCID 25260760HCID 25260760, compoundYield 88%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of tert-butyl 4-(3-(4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-1-(1-(ethoxycarbonyl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl)phenyl)ureido)piperidine-1-carboxylate (0.054 mmol) in CH2Cl2 (1 mL) and trifluoroacetic acid (0.2 mL) is stirred at room temperature for 2 hours, diluted with saturated sodium bicarbonate, extracted with CH2Cl2, washed with brine, dried and concentrated. Purification by HPLC provides ethyl 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-(4-(3-piperidin-4-ylureido)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate (88%). (HRMS=604.3356 (M+H, obs.), 604.3354 (M+H, calc.))

Workup

  1. extractionextracted with CH2Cl2
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated
  5. customPurification by HPLC

Sources & evidence

ORD record
ord-188b86d9235b4cd6b1665bb644364b74
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

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