Diisopropylethylamine → HCID 67086717, compound

HRID 2174975Notes

Reaction equation

HRID 2174975 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([NH:11][CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[N:24]=[C:25]([CH3:31])[S:26][C:27]=1[C:28](O)=[O:29].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>C(OCC)(=O)C.CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C:28]([C:27]3[S:26][C:25]([CH3:31])=[N:24][C:23]=3[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[F:16])=[O:29])[CH2:12]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 18473856HCID 18473856, compoundHCID 43810891Tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate

Product 1

HCID 67086717HCID 67086717, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3,8-Diaza-bicyclo[4.2.0]octane-3-carboxylic acid tert-butyl ester (92 mg, 0.44 mmol), 4-(2-fluoro-phenyl)-2-methyl-thiazole-5-carboxylic acid (104 mg, 0.44 mmol), di-isopropylethylamine (0.25 mL, 1.30 mmol) and HATU (247 mg, 0.65 mmol) were dissolved into DMF (5 mL) and stirred at room temperature for 18 h. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with 1N NaOH (10 mL) and water (2×100 mL). The organic layers were combined, dried, filtered and concentrated to yield the title compound (125 mg, 67%). MS (ESI) mass calcd. for C12H18FN3OS, 431.41; m/z found, 432.3 [M+H]+.

Workup

  1. washwashed with 1N NaOH (10 mL) and water (2×100 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92bb9eb9f96843fa98c69337ceab839b
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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