Dimethylformamide → methyl [2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethyl]carbamate

HRID 1994906Notes

Reaction equation

HRID 1994906 reaction equation
[CH3:1][N:2]([S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:23])=[O:22])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17]C(O)=O)[CH2:15][N:16]=1)=[CH:8]2.[CH2:29]([N:31]([CH2:34]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:43])C=CC=CC=1.CN(C)[CH:55]=[O:56]>C(OCC)(=O)C.CO>[CH3:1][N:2]([S:21]([C:24]1[S:25][CH:26]=[CH:27][CH:28]=1)(=[O:22])=[O:23])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]1[S:13][CH:14]([CH2:17][CH2:29][NH:31][C:34](=[O:43])[O:56][CH3:55])[CH2:15][N:16]=1)=[CH:8]2

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 59135943HCID 59135943, compound

Product 1

HCID 59136096methyl [2-(2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)ethyl]carbamateYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-{7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (40 mg), triethylamine (0.038 mL), diphenylphosphorylazide (0.024 mL) and N,N-dimethylformamide (3 mL) was stirred at room temperature for 1 hr. Methanol (3 mL) was added to the reaction solution, and the mixture was heated at 50° C. for 3 hr. The reaction solution was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3-7:3), and the obtained pale-yellow oil was crystallized from ethyl acetate-hexane to give the title compound (11.7 mg, yield: 28%) as pale-yellow crystals.

Workup

  1. temperaturethe mixture was heated at 50° C. for 3 hr
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe obtained pale-yellow oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-73a5b174ab9f40f6905c177c662a4e29
Source dataset
uspto-grants-2010_01
Patent number
US07652133B2

Reaction notes

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