Isopropanol → HCID 58167981, compound

HRID 1029094Notes

Reaction equation

HRID 1029094 reaction equation
Cl[C:2]1[C:11]2[CH:12]=[CH:13][C:14]([Cl:16])=[CH:15][C:10]=2[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl[C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1F)[NH2:21].[CH:26](O)(C)[CH3:27]>>[Cl:16][C:14]1[CH:13]=[CH:12][C:11]2[C:2]([NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[C:18]([C:26]#[CH:27])[CH:19]=3)=[N:3][C:4]3[C:9]([C:10]=2[CH:15]=1)=[CH:8][CH:7]=[CH:6][N:5]=3

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 97083-Chloro-4-fluoroanilineHCID 58168160HCID 58168160, compound

Product 1

HCID 58167981HCID 58167981, compoundYield 63%

Conditions

Temperature
120 °C

Procedure

6,9-Dichloro-benzo[c][1,8]naphthyridine (20 mg, 0.08 mmol), and 3-chloro-4-fluoroaniline (24 mg, 0.16 mmol) were suspended in isopropanol (2 mL) and stirred overnight at 120° C. The reaction solution was cooled to room temperature, and the resulting precipitate was filtered, washed with isopropanol, and dried under vacuum to provide 57 (18 mg, 63% yield) as a yellow solid. LC-MS (M+H=358, obsd.=358). 1H NMR (400 MHz, d6-DMSO): δ 10.75 (s, 1H), 9.63 (dd, 1H), 9.07 (d, 1H), 8.99 (d, 1H), 8.86 (dd, 1H), 8.33 (dd, 1H), 8.09 (dd, 1H), 8.04 (m, 1H), 7.80 (dd, 1H), 7.52 (t, 1H).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe resulting precipitate was filtered
  3. washwashed with isopropanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-9a07a889a75f41138403fd30f7ae09ac
Source dataset
uspto-grants-2014_05
Patent number
US08735584B2

Reaction notes

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