Dimethylformamide → HCID 67118826, compound

HRID 1188980Notes

Reaction equation

HRID 1188980 reaction equation
[C:1]([Si:5]([C:46]([CH3:49])([CH3:48])[CH3:47])([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[O:6][CH2:7][CH:8]([CH3:39])[O:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25](O)=[O:26])[CH2:22][N:23]=1)=[CH:15]2)([CH3:4])([CH3:3])[CH3:2].Cl.C[N:52](C)CCCN=C=NCC.[NH4+].ON1C2C=CC=CC=2N=N1.CN(C)C=O>CCCCCC.C(OCC)(=O)C.O>[C:1]([Si:5]([C:46]([CH3:48])([CH3:47])[CH3:49])([C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)[O:6][CH2:7][CH:8]([CH3:39])[O:9][C:10]1[CH:11]=[C:12]([O:28][C:29]2[CH:30]=[CH:31][C:32]([S:35]([CH3:38])(=[O:37])=[O:36])=[CH:33][CH:34]=2)[CH:13]=[C:14]2[C:18]=1[NH:17][C:16]([C:19]1[S:20][CH:21]([CH2:24][C:25]([NH2:52])=[O:26])[CH2:22][N:23]=1)=[CH:15]2)([CH3:3])([CH3:4])[CH3:2]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220338091-Hydroxybenzotriazole, ammonium saltHCID 67118530HCID 67118530, compound

Product 1

HCID 67118826HCID 67118826, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2-{7-(2-{[di-tert-butyl(phenyl)silyl]oxy}-1-methylethoxy)-5-[4-(methylsulfonyl)phenoxy]-1H-indol-2-yl]-4,5-dihydro-1,3-thiazol-5-yl)acetic acid (320 mg), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (165 mg), 1-hydroxybenzotriazole ammonium salt (131 mg) and N,N-dimethylformamide (8 mL) was stirred at room temperature for 18 hr. Water was added to the reaction solution, and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtrated, and concentrated under reduced pressure. The obtained crude product was subjected to basic silica gel column chromatography (ethyl acetate:hexane=30:70 to 100:0, volume ratio) to give the title compound (262 mg, yield 55%) as an orange oil. MS 742 (MH+).

Workup

  1. extractionthe mixture was subjected to extraction with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltrated
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained crude product

Sources & evidence

ORD record
ord-be1abaee100d4de48b23d382cc3048f3
Source dataset
uspto-grants-2014_03
Patent number
US08673942B2

Reaction notes

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