Trifluoroacetic acid → 3-(2-hydroxyethyl)-2-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-one

HRID 627803Notes

Reaction equation

HRID 627803 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[N:21]=2)[N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:15]=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[OH:1][CH2:2][CH2:3][CH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[C:14]1[C:22]2[C:17](=[N:18][CH:19]=[C:20]([C:23]3[CH:28]=[CH:27][C:26]([S:29]([CH:32]([CH3:34])[CH3:33])(=[O:31])=[O:30])=[CH:25][CH:24]=3)[N:21]=2)[NH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 711436113-(2-Hydroxyethyl)-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one

Product 1

HCID 711436233-(2-hydroxyethyl)-2-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)isoindolin-1-oneYield 50.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-hydroxyethyl)-2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]isoindolin-1-one (58 mg, 0.08068 mmol) dissolved in DCM (2 mL) under N2 and Et3SiH (64.44 μL, 0.4034 mmol) then TFA (300 μL) added. Reaction mixture stirred overnight, then concentrated and residue azeotroped with DCM (×3). Purified by hplc to give the title compound as a pale yellow solid (19.3 mg, 50%); 1H NMR (400 MHz, DMSO) 1.03 (6H, d), 1.72-1.79 (1H, m), 2.00-2.15 (1H, m), 3.00-3.09 (1H, m), 3.32 (1H, sep), 4.28 (1H, t), 5.82-5.85 (1H, m), 7.42 (1H, t), 7.57 (1H, t), 7.65 (2H, d), 7.80 (2H, d), 8.21 (1H, s), 8.32 (2H, d), 8.93 (1H, s), 12.30 (1H, brs); MS (ES+) 477.0.

Workup

  1. customReaction mixture
  2. concentrationconcentrated
  3. customresidue azeotroped with DCM (×3)
  4. customPurified by hplc

Sources & evidence

ORD record
ord-960b5b59e86f4dc5bc0ddf9b9e787c06
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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