Triethylamine → HCID 86703374, compound

HRID 512535Notes

Reaction equation

HRID 512535 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[N:11][C:10]=2[C:25]([NH2:27])=[O:26])=[O:7])=[CH:4][CH:3]=1.CCN(CC)CC.[C:37]([O:40][CH2:41][C:42](Cl)=[O:43])(=[O:39])[CH3:38]>C1COCC1>[C:37]([O:40][CH2:41][C:42]([NH:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([NH:8][C:9]2[S:13][C:12]([NH:14][C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=3)=[N:11][C:10]=2[C:25]([NH2:27])=[O:26])=[O:7])=[CH:4][CH:3]=1)=[O:43])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 86703375HCID 86703375, compound

Product 1

HCID 86703374HCID 86703374, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 5-(4-aminobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.15 g, 0.37 mmol) and Et3N (0.3 mL, 2.33 mmol) in THF (20 mL) was added acetoxyacetyl chloride (0.12 mL, 1.11 mmol) at 0° C. The mixture was stirred overnight at rt. The solvent was evaporated, and the residue was purified by silica gel column chromatography eluted with 50% EtOAc in hexane to give 0.15 g (80% yield) of the titled compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluted with 50% EtOAc in hexane

Sources & evidence

ORD record
ord-1945af8390044ae281abf2cb6b1847c5
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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