Benzoyl chloride → HCID 19040745, compound

HRID 1683921Notes

Reaction equation

HRID 1683921 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:12]=2)[NH:7][CH:6]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15]3[C:20]([NH:21][C:30]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:37])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH:12]=2)[NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 19040740HCID 19040740, compound

Product 1

HCID 19040745HCID 19040745, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-(2-dimethylaminoethyl)-5-(3-aminopyrid-2-ylamino)-1H-indole (0.157 g, 0.53 mmol) and triethylamine (74 μL, 0.54 mmol, 1.0 eq) in anhydrous tetrahydrofuran (3 mL) was added dropwise benzoyl chloride (62 μL, 0.54 mmol, 1.0 eq). The resulting reaction mixture was stirred at room temperature under nitrogen for 15 minutes. A saturated solution of sodium hydrogen carbonate (10 mL) was added, and this aqueous mixture was extracted with ethyl acetate (3×10 mL). The organic extracts were combined, dried (MgSO4), and evaporated under reduced pressure. The residue was triturated in diethyl ether to afford the title compound (0.082 g, 39%) as an amorphous solid: 13C NMR (DMSO-d6) δ166.5, 151.9, 144.5, 134.5; 132.7, 132.5, 131.6, 128.3, 128.0, 127.2, 122.8, 119.6, 117.3, 113.3, 112.1, 110.8, 110.4, 59.9, 45.0, 23.1; LRMS (m/z, relative intensity) 399 (M+, 100), 354 (33), 249 (10), 235 (18), 204 (40), 160 (86); HRMS calculated for C24H25N5O 399.2062, found 399.2080.

Workup

  1. customThe resulting reaction mixture
  2. extractionthis aqueous mixture was extracted with ethyl acetate (3×10 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe residue was triturated in diethyl ether

Sources & evidence

ORD record
ord-6d953bee3d4f42ba8b5bbd11fd202b28
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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