Ethylamine → 2-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamide

HRID 712280Notes

Reaction equation

HRID 712280 reaction equation
[CH2:1]([NH2:3])[CH3:2].[NH2:4][C:5]1[S:6][C:7]2[C:13]([C:14]([OH:16])=O)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][C:8]=2[N:9]=1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CO.CN(C=O)C.CCOC(C)=O>[NH2:4][C:5]1[S:6][C:7]2[C:13]([C:14]([NH:3][CH2:1][CH3:2])=[O:16])=[CH:12][C:11]([O:17][CH3:18])=[CH:10][C:8]=2[N:9]=1

Participants

8

Reactant 4

HCID 6341EthylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866639922-Amino-5-methoxy-1,3-benzothiazole-7-carboxylic acid

Product 1

HCID 866639932-amino-N-ethyl-5-methoxy-1,3-benzothiazole-7-carboxamideYield 53%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethylamine (2 mL, 4.02 mmol, 2M soln in methanol) was added to a solution of 2-amino-5-methoxy-1,3-benzothiazole-7-carboxylic acid (300 mg, 1.34 mmol), diisopropyl ethylamine (0.93 mL, 5.36 mmol) and HATU (560 mg, 1.47 mmol) in DMF (6 mL). The reaction was stirred at ambient temperature for 2 hours after which time LCMS indicated clean conversion to the product. The reaction was diluted with EtOAc, washed with water and brine then dried (MgSO4), filtered and concentrated in vacuo. The crude material was purified by trituration with DCM to give the product as an off white solid, 178 mg, 53% yield.

Workup

  1. washwashed with water and brine
  2. dry with materialthen dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by trituration with DCM
  6. customto give the product as an off white solid, 178 mg, 53% yield

Sources & evidence

ORD record
ord-07cf3e7fd7844c7e8f8bbb7dc390d79a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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