HCID 86706968, compound → HCID 86706967, compound

HRID 1750297Notes

Reaction equation

HRID 1750297 reaction equation
[F:1][CH:2]([F:34])[C:3]1[N:17](COCC[Si](C)(C)C)[C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]=2[C:4]=1[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30]>FC(F)(F)C(O)=O>[F:34][CH:2]([F:1])[C:3]1[NH:17][C:6]2[N:7]=[CH:8][N:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]=2[C:4]=1[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[C:29]#[N:30]

Participants

3

Reactant 1

HCID 86706968HCID 86706968, compound

Product 1

HCID 86706967HCID 86706967, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-[6-(difluoromethyl)-4-(morpholin-4-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-5-yl]benzonitrile (C31) (10 mg, 21 μmol) in trifluoroacetic acid (2 mL) was stirred at room temperature for 24 hours. The reaction mixture was concentrated and purified by preparative reversed phase high-performance liquid chromatography (Column: DIKMA Diamonsil(2) C18, 5 μm; Eluent: 22% acetonitrile in water containing 0.225% formic acid) to provide the product as a white solid. Yield: 2.0 mg, 5.6 μmol, 27%. LCMS m/z 355.9 [M+H+]. 1H NMR (400 MHz, DMSO-d6) δ 13.06 (brs, 1H), 8.47 (s, 1H), 7.92 (ddd, J=6.7, 2.1, 1.7 Hz, 1H), 7.83-7.85 (m, 1H), 7.69-7.76 (m, 2H), 7.02 (t, JHF=52.5 Hz, 1H), 3.22-3.30 (m, 4H), 3.03-3.10 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by preparative reversed phase high-performance liquid chromatography (Column: DIKMA Diamonsil(2) C18, 5 μm; Eluent: 22% acetonitrile in water containing 0.225% formic acid)

Sources & evidence

ORD record
ord-58e6e67df56043588b4ce06f1fc55e71
Source dataset
uspto-grants-2015_10
Patent number
US09156845B2

Reaction notes

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