Diisopropylethylamine → HCID 59128871, compound

HRID 1991387Notes

Reaction equation

HRID 1991387 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8]2[C:9]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([CH3:24])([CH3:23])[CH3:22])=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:4][C:3]=1[C:25]([F:28])([F:27])[F:26].[O:29](C(OC(C)(C)C)=O)[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=O.CCN(C(C)C)C(C)C>CN(C1C=CN=CC=1)C.C1COCC1>[Br:1][C:2]1[S:6][C:5]([N:7]([C:8]2[C:9]([O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:21]([CH3:24])([CH3:22])[CH3:23])=[N:10][CH:11]=[CH:12][CH:13]=2)[C:30](=[O:29])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[N:4][C:3]=1[C:25]([F:27])([F:26])[F:28]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 59128919HCID 59128919, compound

Product 1

HCID 59128871HCID 59128871, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-(5-bromo-4-(trifluoromethyl)thiazol-2-yl)-2-(2-tert-butylphenoxy)pyridin-3-amine (Example 323a, 135 mg, 0.29 mmol), BOC2O (75 mg, 0.34 mmol), DMAP (5 mg) and DIPEA (59 μl, 0.34 mmol) in THF (5 mL) was stirred at rt for 5 h. The solvent was removed and the residue was purified by flash chromatography (silica, 0-50% EtOAc/hexane gradient) provided Example A125a (149 mg) as a white foam. (M+H)+═574.2.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified by flash chromatography (silica, 0-50% EtOAc/hexane gradient)
  3. customprovided Example A125a (149 mg) as a white foam

Sources & evidence

ORD record
ord-655eedb8b71a47698db50bd5ef9aaa89
Source dataset
uspto-grants-2010_01
Patent number
US07645778B2

Reaction notes

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