2-Amino-6-methoxybenzothiazole → HCID 25263590, compound

HRID 222372

Reaction equation

HRID 222372 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([OH:18])=O)[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:19][C:20]1[S:21][C:22]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:23]=2[N:24]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([C:16]([NH:19][C:20]3[S:21][C:22]4[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:23]=4[N:24]=3)=[O:18])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 156302-Amino-6-methoxybenzothiazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 550298731-(3,4-dichlorobenzyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid2×

Product 1

HCID 25263590HCID 25263590, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxylic acid (Intermediate 4) (0.1 g, 0.35 mmol), 2-amino-6-methoxybenzothiazole (0.062 g, 0.35 mmol), HATU (0.082 g, 0.45 mmol) and DIPEA (85 μL, 0.45 mmol) in DMF (5 mL) was stirred at 45° C. for 3 days. The solvent was evaporated and the residue was washed with water and extracted with DCM. The organic phase was dried over sodium sulphate, filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with DCM/MeOH (99/1) to give after trituration in diisopropyl ether, the title compound as a white solid (15 mg, 10%). HRMS calculated for C19H15Cl2N5O2S (M+H)+ 448.0402, found: 448.0403, Rt: 3.31 min. MP: 225° C.

Workup

  1. customThe solvent was evaporated
  2. washthe residue was washed with water
  3. extractionextracted with DCM
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with DCM/MeOH (99/1)
  9. customto give after trituration in diisopropyl ether

Sources & evidence

ORD record
ord-e4ca3c39296d4d8b99777e28e5bd05e5
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Linked notes

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