4-Chlorobenzoic Acid → HCID 69379171, compound

HRID 381401Notes

Reaction equation

HRID 381401 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH3:12])=[C:6]2CCN.[CH3:16][CH2:17]N=C=NCCCN(C)C.Cl.[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.O>[Cl:28][C:29]1[CH:37]=[CH:36][C:32]([C:33]([N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[CH3:12])=[O:34])=[CH:31][CH:30]=1.[CH2:16]([C:37]1[CH:36]=[C:32]([CH:31]=[CH:30][C:29]=1[Cl:28])[C:33]([NH2:8])=[O:35])[CH3:17]

Participants

7

Reactant 3

HCID 63184-Chlorobenzoic AcidHCID 528992-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69379171HCID 69379171, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A reaction mixture containing Compound 7 oxalate salt (520 mg, 2.55 mmol), EDCl (489 mg, 2.55 mmol), DMAP (31 mg, 0.255 mmol), and 4-chlorobenzoic acid (354 mg, 2.26 mmol) in anhydrous methylene chloride (15 mL) was stirred at rt for 3 hours. The reaction mixture was diluted with water and extracted with CH2Cl2 (2×15 mL). The combined CH2Cl2 extracts were washed with water, dried (MgSO4), filtered, and the solvent concentrated in vacuo. The crude amide was chromatographed on silica gel (EtOAc:hexanes; 25:75 then 60:40) to afford the precursor amide Compound 8e as a yellow oil (390 mg, 45%), which was used in the next step without any further characterization owing to its unstable nature.

Workup

  1. extractionextracted with CH2Cl2 (2×15 mL)
  2. washThe combined CH2Cl2 extracts were washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationthe solvent concentrated in vacuo
  6. customThe crude amide was chromatographed on silica gel (EtOAc

Sources & evidence

ORD record
ord-efbf90e5a65b4d2195a96c2145daa490
Source dataset
uspto-grants-2001_10
Patent number
US06306890B1

Reaction notes

Loading…