Ethanolamine → HCID 68686374, compound

HRID 1159100Notes

Reaction equation

HRID 1159100 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:15]=[CH:14][C:6]2[CH2:7][CH:8]3[CH2:13][N:9]3[S:10](=[O:12])(=[O:11])[C:5]=2[CH:4]=1.[CH2:18]([CH2:20][NH2:21])[OH:19].C(N(CC)CC)C>O1CCCC1>[OH:19][CH2:18][CH2:20][NH:21][CH2:13][CH:8]1[CH2:7][C:6]2[CH:14]=[CH:15][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][C:5]=2[S:10](=[O:12])(=[O:11])[NH:9]1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8471TriethylamineHCID 86597542HCID 86597542, compound

Product 1

HCID 68686374HCID 68686374, compoundYield 147.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 8,8a-dihydro-5-(trifluoromethyl)-1H-azirino[1,2-b][1,2]benzothiazine 3,3-dioxide (685 mg, 0.260 mmol), ethanolamine (0.785 mL, 13.0 mmol) and triethylamine (0.33 mL, 2.6 mmol) in tetrahydrofuran (25 mL) was heated in a sealed tube at 100° C. for 3 h. The cooled reaction was concentrated in vacuo. The residue was chromatographed (silica, 2%-20% methanol/dichloromethane gradient) to provide 3,4-dihydro-N-(2-hydroxyethyl)-7-(trifluoromethyl)-2H-1,2-benzothiazine-3-methanamine 1,1-dioxide as a white solid (124 mg) and additional impure material: LCMS (neg. ion spectrum) m/z 323.

Workup

  1. customThe cooled reaction
  2. concentrationwas concentrated in vacuo
  3. customThe residue was chromatographed (silica, 2%-20% methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-88b01300306f417eb108cc2b54d58a22
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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