Triethylamine → HCID 46182187, compound

HRID 386479Notes

Reaction equation

HRID 386479 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.[CH3:25][N:26]1[C:30]([C:31](O)=[O:32])=[CH:29][N:28]=[CH:27]1.Cl.CN(C)CCCN=C=NCC.SC1SC2C=CC=CC=2N=1.C(N(CC)CC)C>C(#N)C>[C:12]1([S:9]([N:8]([CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:4]2[CH:3]=[C:2]([NH:1][C:31]([C:30]3[N:26]([CH3:25])[CH:27]=[N:28][CH:29]=3)=[O:32])[CH:7]=[CH:6][CH:5]=2)(=[O:11])=[O:10])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27735071-methyl-1H-imidazole-5-carboxylic acidHCID 21708006HCID 21708006, compoundHCID 178418395HCID 178418395, compound

Product 1

HCID 46182187HCID 46182187, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-(3-amino-phenyl)-N-benzyl-benzene sulfonamide (25 mg, 0.07 mmol), 3-methyl-3H-imidazole-4-carboxylic acid (14 mg, 0.11 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (16 mg, 0.08 mmol), mercaptobenzothiazole (2 mg, 0.007 mmol) and triethylamine (25 μl, 0.18 mmol) in dry acetonitrile (1 ml) were stirred at room temperature for 15 hrs. The reaction mixture was quenched with water (10 ml), extracted with dichloromethane (3×7 ml) and the combined organics concentrated in vacuo. The crude residue was purified by preparative TLC (SiO2) eluting with ethyl acetate/dichloromethane (1:1) to afford the title compound as an off white solid (2.8 mg, 8%). HPLC retention time 5.6 min. Mass spectrum (ES+) m/z 447 (M+H).

Workup

  1. customThe reaction mixture was quenched with water (10 ml)
  2. extractionextracted with dichloromethane (3×7 ml)
  3. concentrationthe combined organics concentrated in vacuo
  4. customThe crude residue was purified by preparative TLC (SiO2)
  5. washeluting with ethyl acetate/dichloromethane (1:1)

Sources & evidence

ORD record
ord-e00c7e21fd064790b95a0b842f40bb18
Source dataset
uspto-grants-2013_02
Patent number
US08372840B2

Reaction notes

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