Triethylamine → HCID 178484626, compound

HRID 1604671Notes

Reaction equation

HRID 1604671 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:30][C:31]([OH:33])=O)=[CH:26][CH:27]=5)[C:22]([C:34]5[NH:38][N:37]=[N:36][N:35]=5)=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:39](N1C=CN=C1)([N:41]1C=CN=[CH:42]1)=O.Cl.CNC.C(N(CC)CC)C>ClCCl>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][N:20]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH2:30][C:31](=[O:33])[N:41]([CH3:42])[CH3:39])=[CH:26][CH:27]=5)[C:22]([C:34]5[NH:38][N:37]=[N:36][N:35]=5)=[CH:21]4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 682631,1'-CarbonyldiimidazoleHCID 178441407HCID 178441407, compound

Product 1

HCID 178484626HCID 178484626, compoundYield 47.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(carboxymethoxy)indol-3-yl}-1H-tetrazole (60 mg) and 1,1'-carbonyldiimidazole (60 mg) in dichloromethane (2 ml) was stirred at room temperature for 5 hours. And then, dimethylamine hydrochloride (16.5 mg) and triethylamine (0.5 ml) were added to the mixture successively. After being stirred for 18 hours, the mixture was concentrated under reduced pressure. The resulting residue was acidified with diluted hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel and eluted with a mixture of chloroform, ethyl acetate and methanol. The fractions containing the objective compound were combined and concentrated under reduced pressure to give 5-{1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-(N,N-dimethylcarbamoylmethoxy)indol-3-yl}-1H-tetrazole (30.1 mg).

Workup

  1. stirringAfter being stirred for 18 hours
  2. concentrationthe mixture was concentrated under reduced pressure
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a mixture of chloroform, ethyl acetate and methanol
  8. additionThe fractions containing the objective compound
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19849cd5dea24c269c35c6f2d74fbe81
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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