HCID 59026385, compound → HCID 178482940, compound

HRID 1865697Notes

Reaction equation

HRID 1865697 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][C:30]([F:33])([F:32])[F:31])=[N:21][N:20](COCC[Si](C)(C)C)[C:17]3=[N:18][CH:19]=2)=[CH:10][C:9]=1[C:42]([N:44]1[CH2:48][CH2:47][CH:46]([N:49]([CH3:51])[CH3:50])[CH2:45]1)=[O:43])(C)(C)C>C(O)(=O)C.SCC(O)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][C:30]([F:33])([F:32])[F:31])=[N:21][NH:20][C:17]3=[N:18][CH:19]=2)=[CH:10][C:9]=1[C:42]([N:44]1[CH2:48][CH2:47][CH:46]([N:49]([CH3:51])[CH3:50])[CH2:45]1)=[O:43]

Participants

4

Reactant 1

HCID 59026385HCID 59026385, compound

Product 1

HCID 178482940HCID 178482940, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1133Thioglycolic AcidSolvent

Procedure

{2-(3-Dimethylaminopyrrolidine-1-carbonyl)-4-[3-(2-trifluoromethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-carbamic acid tert-butyl ester (220 mg, 0.3 mmol) was dissolved in 1 ml of 5% v/v of 70% perchlroric acid in glacial acetic acid containing 0.4 ml of mercaptoacetic acid and the resulting mixture stirred overnight at room temperature. The crude was filtered over a 0.45 μm PTFE syringe filter and directly purified by mass-triggered reverse phase HPLC to afford {2-amino-5[3-(2-trifluoromethoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-dimethylamino-pyrrolidin-1-yl)-methanone. 1H NMR (500 MHz, DMSO-d6) δ 1.65 (m, 1H), 1.92-2.02 (m, 7H), 3.15-3.68 (m, 5H), 5.45 (s, 2H), 6.78 (d, 1H), 7.45 (m, 2H), 7.50-7.58 (m, 3H), 7.88, (d, 1H), 8.18 (s, 1H), 8.66 (s, 1H). MS: m/z 511.2 (M+H+).

Workup

  1. filtrationThe crude was filtered over a 0.45 μm PTFE syringe
  2. filtrationfilter
  3. customdirectly purified by mass-triggered reverse phase HPLC

Sources & evidence

ORD record
ord-1b9bf5a312044a01973153867154d1eb
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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