Ethyl Acetate → HCID 178508364, compound

HRID 389608Notes

Reaction equation

HRID 389608 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:22]=[N:23][N:24]([C@H:26]3[CH2:31][CH2:30][C@H:29]([O:32][Si](C(C)(C)C)(C)C)[CH2:28][CH2:27]3)[CH:25]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][NH:16][C:17]4=[O:20])=[CH:13][CH:12]=3)[O:8][C:7]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOC(C)=O>C1COCC1>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:21]2[CH:22]=[N:23][N:24]([C@H:26]3[CH2:27][CH2:28][C@H:29]([OH:32])[CH2:30][CH2:31]3)[CH:25]=2)=[C:6]2[CH:10]=[C:9]([C:11]3[CH:19]=[C:18]4[C:14]([CH2:15][NH:16][C:17]4=[O:20])=[CH:13][CH:12]=3)[O:8][C:7]=12

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 178455331HCID 178455331, compound

Product 1

HCID 178508364HCID 178508364, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-{7-amino-4-[1-(trans-4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-1H-pyrazol-4-yl]furo[2,3-c]pyridin-2-yl}-2,3-dihydro-1H-isoindol-1-one in THF (2.4 mL) was added tetra-n-butylammonium fluoride (1.0 M in THF, 2.4 mL, 2.4 mmol). After 4 h, the reaction was diluted into EtOAc and washed with sodium bicarbonate and water. The aqueous layer was concentrated. The residual solid was rinsed with MeOH and EtOAc thoroughly, then purified by ISCO chromatography (0 to 10% 7 N NH3/MeOH:EtOAc) to afford 1.5 mg (3%) of the title compound. 1H NMR (400 MHz, CD3OD): δ 8.44 (s, 1H), 8.34 (d, J=7.8 Hz, 1H), 8.16 (s, 1H), 7.92 (d, J=5.3 Hz, 2 H), 7.76 (d, J=8.1 Hz, 1H), 7.63 (s, 1H), 4.56-4.58 (m, 2H), 4.23-4.34 (m, 1H), 3.67-3.78 (m, 1H), 2.11-2.25 (m, 4H), 1.97-2.08 (m, 2H), 1.54 (m, 2H); MS (ESI): 430.17 [M+H]+; HPLC tR=0.90 min (TOF: polar—3 min).

Workup

  1. washwashed with sodium bicarbonate and water
  2. concentrationThe aqueous layer was concentrated
  3. washThe residual solid was rinsed with MeOH and EtOAc thoroughly
  4. custompurified by ISCO chromatography (0 to 10% 7 N NH3/MeOH:EtOAc)

Sources & evidence

ORD record
ord-09961371bd5047329516c5308885ea68
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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