Triethylamine → HCID 68569865, compound

HRID 18742Notes

Reaction equation

HRID 18742 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:10]=[C:9]1[NH2:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:6]([N:8]1[C@H:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:10]=[C:9]1[NH:25][C:38](=[O:39])[C:37]1[CH:41]=[CH:42][C:34]([F:33])=[CH:35][CH:36]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 68569815HCID 68569815, compound

Product 1

HCID 68569865HCID 68569865, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 124 (200 mg, 0.593 mmol), triethylamine (0.082 mL, 0.583 mmol), 4-dimethylaminopyridine (10 mg), and 4-fluorobenzoyl chloride (0.063 mL, 0.533 mmol) in dichloromethane (2 mL) is stirred at RT for 0.5 h. The solution is diluted with dichloromethane and washed with NaHCO3, brine, and then dried (MgSO4). The mixture is filtered, the filtrate evaporated, and residue purified by chromatography on silica gel; gradient elution with heptane:EtOAc (70:30-60:40) gives 123 mg of the product 125. 1H NMR (CDCl3) δ 10.00 (s, 1 H), 8.50-8.35 (m, 2 H), 7.20-6.85 (m, 12 H), 6.55-6.40 (m, 2 H), 1.20 (s, 9 H); MS: m/z 460 (M++1).

Workup

  1. washwashed with NaHCO3, brine
  2. dry with materialdried (MgSO4)
  3. filtrationThe mixture is filtered
  4. customthe filtrate evaporated
  5. customresidue purified by chromatography on silica gel
  6. washgradient elution with heptane:EtOAc (70:30-60:40)

Sources & evidence

ORD record
ord-5239b86b416f4e7aa19bbf9bc8be47e8
Source dataset
uspto-grants-2010_06
Patent number
US07741493B2

Reaction notes

Loading…