Ethanolamine → HCID 86703391, compound

HRID 512560Notes

Reaction equation

HRID 512560 reaction equation
F[C:2]1[CH:31]=[CH:30][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](OCC)=[O:26])=[O:7])=[CH:4][CH:3]=1.[NH2:32][CH2:33][CH2:34][OH:35]>CN1C(=O)CCC1.CCOC(C)=O>[OH:35][CH2:34][CH2:33][NH:32][C:25]([C:10]1[N:11]=[C:12]([NH:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[S:13][C:9]=1[NH:8][C:6](=[O:7])[C:5]1[CH:30]=[CH:31][C:2]([NH:11][CH2:10][CH2:25][OH:26])=[CH:3][CH:4]=1)=[O:26]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 86703390HCID 86703390, compound

Product 1

HCID 86703391HCID 86703391, compoundYield 47.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of Ethyl 5-(4-fluorobenzamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxylate (25 mg, 0.06 mmol) and 2-aminoethanol (0.024 mL, 0.40 mmol) in NMP (0.5 mL) was treated using a microwave synthesizer for 70 min (Biotage, 150° C.). The reaction mixture was diluted with EtOAc. The organic layer was washed with H2O, dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel chromatography eluted with 2.5% MeOH in DCM to give 7 mg (25% yield) of the titled compound.

Workup

  1. customfor 70 min
  2. custom(Biotage, 150° C.)
  3. washThe organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by silica gel chromatography
  7. washeluted with 2.5% MeOH in DCM

Sources & evidence

ORD record
ord-a565d8a2bf1543afb09b63e1d92f1521
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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