HCID 57975902, compound → HCID 178489399, compound

HRID 1865652Notes

Reaction equation

HRID 1865652 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13](=[O:51])[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[N:28][N:27](COCC[Si](C)(C)C)[C:24]3=[N:25][CH:26]=2)=[CH:17][C:16]=1[C:46](=[O:50])[N:47]([CH3:49])[CH3:48])=O)(C)(C)C>Cl(O)(=O)(=O)=O.C(O)(=O)C>[CH3:49][N:47]([CH3:48])[C:46]([C:16]1[CH:17]=[C:18]([C:21]2[CH:22]=[C:23]3[C:29]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[O:36][CH3:37])=[N:28][NH:27][C:24]3=[N:25][CH:26]=2)[CH:19]=[CH:20][C:15]=1[NH:14][C:13]([CH:9]1[CH2:10][CH2:11][CH2:12][NH:8]1)=[O:51])=[O:50]

Participants

4

Reactant 1

HCID 57975902HCID 57975902, compound

Product 1

HCID 178489399HCID 178489399, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24247Perchloric AcidSolvent

Procedure

2-{2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenylcarbamoyl}-pyrrolidine-1-carboxylic acid tert-butyl ester (103 mg, 0.14 mmol) obtained in step 1 was dissolved in 1 ml of a 5% v/v solution of 70% perchloric acid in acetic acid and stirred overnight at room temperature. The crude was filtered and purified by reverse phase HPLC, lyophilized to afford pyrrolidine-2-carboxylic acid {2-dimethylcarbamoyl-4-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-amide (24 mg, 35% yield). 1H NMR (500 MHz, DMSO-d6) δ 1.76 (m, 2H), 1.91 (m, 1H), 2.19 (m, 1H), 2.89 (m, 1H), 2.95 (d, 6H), 3.01 (m, 1H), 3.10 (m, 1H), 3.85 (s, 3H), 7.10 (m, 1H), 7.22 (d, 1H), 7.47 (m, 1H), 7.65 (d, H), 7.72 (s, 1H), 7.83 (d, 1H), 7.96 (m, 1H), 8.36 (s, 1H), 8.88 (s, 1H). MS: m/z 485.1 (M+H+).

Workup

  1. filtrationThe crude was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ccc3f0bc330348258967d176b4ab3318
Source dataset
uspto-grants-2009_12
Patent number
US07626021B2

Reaction notes

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