1,2-Dichloroethane → HCID 11848594, compound

HRID 1671608Notes

Reaction equation

HRID 1671608 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[C:11]([CH2:21][C:22]([OH:24])=O)[C:12](=[O:20])[N:13]([CH2:15][C:16]([F:19])([F:18])[F:17])[CH:14]=1.Cl.Cl.[O:27]=[C:28]1[NH:36][C:31]2=[N:32][CH:33]=[CH:34][CH:35]=[C:30]2[N:29]1[CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH2:21][C:22]([N:40]2[CH2:39][CH2:38][CH:37]([N:29]3[C:30]4[C:31](=[N:32][CH:33]=[CH:34][CH:35]=4)[NH:36][C:28]3=[O:27])[CH2:42][CH2:41]2)=[O:24])[C:12](=[O:20])[N:13]([CH2:15][C:16]([F:17])([F:18])[F:19])[CH:14]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 181649HOAtHCID 516892Sodium BicarbonateHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 67343425HCID 67343425, compound

Product 1

HCID 11848594HCID 11848594, compoundYield 50.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (410 μL, 2.94 mmol) was added to a solution of [5-bromo-2-oxo-1-(2,2,2-trifluoroethyl)-1,2-dihydropyridin-3-yl]acetic acid (231 mg, 0.736 mmol), 2-oxo-1-(4-piperidinyl)-2,3-dihydro-1H-imidazo[4,5-b]pyridine dihydrochloride (236 mg, 0.809 mmol), EDC (212 mg, 1.10 mmol), and HOAt (100 mg, 0.736 mmol) in DMF (13 mL). After 24 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with ethyl acetate (3×). The organic layers were dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography [100% dichloromethane→90% dichloromethane/methanol] gave the title compound (0.192 g). MS 516.0 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×)
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography [100% dichloromethane→90% dichloromethane/methanol]

Sources & evidence

ORD record
ord-7a8e509b118946b198f95caff6d59d74
Source dataset
uspto-grants-2011_08
Patent number
US07994325B2

Reaction notes

Loading…