Diisopropylethylamine → HCID 42606795, compound

HRID 222379Notes

Reaction equation

HRID 222379 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][N:10]2[C:14]([CH3:15])=[C:13]([NH2:16])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:17][O:18][C:19]1[CH:30]=[CH:29][C:22]2[N:23]=[C:24]([C:26](N)=[O:27])[S:25][C:21]=2[CH:20]=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]([NH:16][C:26]([C:24]3[S:25][C:21]4[CH:20]=[C:19]([O:18][CH3:17])[CH:30]=[CH:29][C:22]=4[N:23]=3)=[O:27])[N:12]=[N:11]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5392826-Methoxybenzothiazole-2-carboxamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59583427HCID 59583427, compound2×

Product 1

HCID 42606795HCID 42606795, compound

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-triazol-4-amine (Intermediate 19) (0.1 g, 0.39 mmol), 6-(methyloxy)-1,3-benzothiazole-2-carboxamide (81 mg, 1 eq), HATU (0.192 g, 1.3 eq) and DIPEA (0.12 mL, 1.3 eq) in DMF (5 mL) was stirred at 45° C. for 48 hours. 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. The residue was purified by flash chromatography eluting with DCM/MeOH (99/1) to give after recrystallisation from acetonitrile the title compound as pink pale crystals (110 mg, 65%). HRMS calculated for C19H15Cl2N5O2S (M+H)+448.0402, found: 448.0406, Rt: 3.08 min. MP: 176° 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
  7. customThe residue was purified by flash chromatography
  8. washeluting with DCM/MeOH (99/1)
  9. customto give
  10. customafter recrystallisation from acetonitrile the title compound as pink pale crystals (110 mg, 65%)

Sources & evidence

ORD record
ord-831e2ba1f1bb42c7b1cfdc89e6a090ca
Source dataset
uspto-grants-2012_06
Patent number
US08207204B2

Reaction notes

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