Acetonitrile → HCID 25269522, compound

HRID 1672533Notes

Reaction equation

HRID 1672533 reaction equation
Cl[C:2]1[O:3][C:4]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][C:9]=2[F:18])=[C:5]([CH3:7])[N:6]=1.[C:19](#[N:21])[CH3:20]>>[F:18][C:9]1[CH:10]=[C:11]([C:14]([F:17])([F:16])[F:15])[CH:12]=[CH:13][C:8]=1[C:4]1[O:3][C:2]([NH:21][C:19]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:20]=2[CH2:5][CH:4]([OH:3])[CH2:8][CH2:9]3)=[N:6][C:5]=1[CH3:7]

Participants

3

Reactant 2

HCID 6342AcetonitrileHCID 66696589HCID 66696589, compound

Product 1

HCID 25269522HCID 25269522, compoundYield 14%

Procedure

A mixture of Example 5D (1.32 g, 4.72 mmol) and Example 1A (1.31 g, 4.72 mmol) in acetonitrile (16 mL) was heated at 150° C. in a microwave reactor for 20 minutes. The solution was cooled and concentrated, and the crude material was chromatographed on silica gel (1 to 20% methanol-CH2Cl2 eluant). The resulting crude product was further purified by trituration with 1:1 hexane-ether, which yielded 0.278 g (14% yield) of the title compound as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 9.23 (s, 1H), 7.64-7.76 (m, 3H), 7.51 (m, 1H), 7.10 (t, J=7.8 Hz, 1H), 6.87 (m, 1H), 4.79 (d, J=4.0 Hz, 1H), 3.91 (m, 1H), 2.67-2.98 (m, 3H), 2.52 (m, 1H), 2.18 (s, 3H), 1.86 (m, 1H), 1.61 (m, 1H). MS (ESI+) m/z 407 (M+H)+, 429 (M+Na)+. Anal Calcd for C21H18F4N2O2: C, 62.07; H, 4.46; N, 6.89. Found: C, 61.90; H, 4.37; N, 6.85.

Workup

  1. customwas heated at 150° C. in a microwave reactor for 20 minutes
  2. temperatureThe solution was cooled
  3. concentrationconcentrated
  4. customthe crude material was chromatographed on silica gel (1 to 20% methanol-CH2Cl2 eluant)
  5. customThe resulting crude product was further purified by trituration with 1:1 hexane-ether, which

Sources & evidence

ORD record
ord-ff9cb82a04f5488ea75f4b789b2f4e6b
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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