Dimethylformamide → HCID 57476313, compound

HRID 1960507Notes

Reaction equation

HRID 1960507 reaction equation
[CH3:1][N:2]([S:21]([C:24]1[S:25][CH:26]=[CH:27][N: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:18](O)=[O:19])[CH2:15][N:16]=1)=[CH:8]2.Cl.C[N:31](C)CCCN=C=NCC.CN(C)C=O>C(OCC)(=O)C.O>[CH3:1][N:2]([S:21]([C:24]1[S:25][CH:26]=[CH:27][N: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:18]([NH2:31])=[O:19])[CH2:15][N:16]=1)=[CH:8]2

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59135783HCID 59135783, compound

Product 1

HCID 57476313HCID 57476313, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-{7-[methyl(1,3-thiazol-2-ylsulfonyl)amino]-1H-indol-2-yl}-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (250 mg), 1H-1,2,3-benzotriazol-1-ol-ammonia complex (114 mg), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (144 mg) and N,N-dimethylformamide (10 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (100 mL) and water (100 mL), and the organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained solid was washed with ethyl acetate to give the title compound (166 mg, yield 67%) as a white solid. melting point 216-218° C.

Workup

  1. washthe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-bf812ea29f154c68be145a796e69e5a1
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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