Dimethylamine, hydrochloride → HCID 67178126, compound

HRID 2362230Notes

Reaction equation

HRID 2362230 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[CH2:5][CH2:6][C:7]1[N:8]([C:20]2[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][C:21]=2[CH3:29])[C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)[CH3:2].[CH3:31][N:32](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.Cl.CNC>C(Cl)Cl.CCOC(C)=O>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[N:8]([C:20]3[CH:28]=[CH:27][C:23]([C:24](=[O:25])[NH:32][CH3:31])=[CH:22][C:21]=3[CH3:29])[C:7]([CH2:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:30])=[CH:11][CH:10]=2)=[CH:13][CH:14]=1

Participants

7

Reactant 4

HCID 10473Dimethylamine, hydrochlorideHCID 199401P,P-Diphenylphosphinic azideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 67179880HCID 67179880, compound

Product 1

HCID 67178126HCID 67178126, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(2-(3-Ethoxy-3-oxopropyl)-5-(4-methoxyphenyl)-1H-pyrrol-1-yl)-3-methylbenzoic acid (44 mg) was treated with TBTU (42 mg), DPPA (10 μL) and dimethylamine HCl (14 mg) in DCM (4 mL) over 8 h at room temperature. The reaction mixture was diluted with EtOAc (15 mL), washed with 0.5 N HCl (8 mL), saturated NaHCO3 (8 mL), and Brine (8 mL). After removal of solvents, the residue was purified by flash silica gel chromatography to afford ethyl 3-(5-(4-methoxyphenyl)-1-(2-methyl-4-(methylcarbamoyl)phenyl)-1H-pyrrol-2-yl)propanoate (25 mg).

Workup

  1. washwashed with 0.5 N HCl (8 mL), saturated NaHCO3 (8 mL), and Brine (8 mL)
  2. customAfter removal of solvents
  3. customthe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-dcdde7bf840e456b9efe2024a9d764fb
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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