Dimethylformamide → HCID 24764717, compound

HRID 911792Notes

Reaction equation

HRID 911792 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[N:13]=[CH:12][C:11]([S:14][C:15]3[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=3)=[CH:10][C:9]=2[O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[S:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:37][CH2:38][N:39]1[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1.CN(C=O)C>O>[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8]2[C:9]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:10][C:11]([S:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:37][CH2:38][N:39]4[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]4)[CH:16]=3)=[CH:12][N:13]=2)[S:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 24764714HCID 24764714, compound

Product 1

HCID 24764717HCID 24764717, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(6-(4-methylthiazol-2-ylamino)-5-phenoxypyridin-3-ylthio)phenol (prepared according to Example 57; 70.0 mg, 0.172 mmol), potassium carbonate (71.2 mg, 0.515 mmol), 1-(2-chloroethyl)piperidine hydrochloride (31.6 mg, 0.172 mmol), and DMF (2 mL) was stirred at room temperature for 30 minutes and heated to 50° C. overnight. The reaction was cooled to room temperature and water (15 mL) was added and extracted with ether. A white precipitate formed in the ether layer and was filtered to afford N-(4-methylthiazol-2-yl)-3-phenoxy-5-(3-(2-(piperidin-1-yl)ethoxy)phenylthio)pyridin-2-amine (34.2 mg, 38.4% yield) as a white solid. 1H NMR (d6-DMSO) δ 9.56 (s, 1H), 8.29 (dd, 1H), 7.50 (dd, 1H), 7.28 (m, 2H), 7.11 (t, 1H), 7.00 (t, 1H), 6.82 (m, 2H), 6.65 (m, 1H), 6.58 (m, 1H), 6.54 (m, 1H), 6.35 (m, 1H), 3.79 (t, 2H), 2.23 (s, 3H), 2.17 (m, 4H), 2.12 (t, 2H), 1.38 (m, 4H), 1.31 (m, 2H); Mass spectrum (esi) m/z=519.1 (M+H).

Workup

  1. temperatureheated to 50° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with ether
  4. customA white precipitate formed in the ether layer
  5. filtrationwas filtered

Sources & evidence

ORD record
ord-6066de3628b64020ac7d83e49a4462f9
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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