Pyridine → HCID 67443712, compound

HRID 1400887Notes

Reaction equation

HRID 1400887 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:16]=[C:17]([I:19])[S:18][C:11]=12)[NH2:5].[N:20]1[CH:25]=[CH:24][CH:23]=C[CH:21]=1.ClC(OC1C=CC=CC=1)=[O:28].C1(N)CC1>CN(C=O)C.O>[CH:25]1([NH:20][C:21]([NH:5][C:4]2[CH:6]=[CH:7][C:8]([O:9][C:10]3[CH:15]=[CH:14][N:13]=[C:12]4[CH:16]=[C:17]([I:19])[S:18][C:11]=34)=[C:2]([F:1])[CH:3]=2)=[O:28])[CH2:23][CH2:24]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 69828CyclopropylamineHCID 584749503-Fluoro-4-((2-iodothieno[3,2-b]pyridin-7-yl)oxy)aniline

Product 1

HCID 67443712HCID 67443712, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of amine 268 (1.7 g, 3.98 mmol) in DMF (7 mL) was added pyridine (0.55 mL, 6.77 mmol) at RT and the resultant solution was stirred for 10 min under Ar atmosphere. Phenyl chloroformate (0.75 mL, 5.97 mmol) was added at 0° C. and the mixture was stirred at RT for 40 min. Cyclopropylamine (1.1 mL, 15.9 mmol) was added to the mixture, and the reaction mixture was warmed to 50° C. and stirred for 2 hours. The mixture was then cooled to RT then poured into water (150 mL) and stirred for 30 min. The precipitate was collected by filtration, washed with water and dried. The crude product was triturated with EtOActo afford title compound 269 (1.75 g, 86% yield) as a pale-violet solid. 1H NMR (300 MHz, DMSO-d6) δ (ppm): 8.70 (br, 1H), 8.45 (d, J=5.4 Hz, 1H), 7.91 (s, 1H), 7.72 (dd, J=13.5, 2.4 Hz, 1H), 7.35 (t, J=9.0 Hz, 1H), 7.23 (m, 1H), 6.62 (d, J=5.4 Hz, 1H), 6.56 (br, 1H), 2.60-2.40 (m, 1H), 0.70-0.60 (m, 2H), 0.48-0.35 (m, 2H).

Workup

  1. temperaturethe reaction mixture was warmed to 50° C.
  2. stirringstirred for 2 hours
  3. temperatureThe mixture was then cooled to RT
  4. stirringstirred for 30 min
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe crude product was triturated with EtOActo

Sources & evidence

ORD record
ord-832b61cbea47458a9738c4e157894793
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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