Diisopropylethylamine → HCID 136038633, compound

HRID 2390511Notes

Reaction equation

HRID 2390511 reaction equation
[C:1]([C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:16][C:17]([C:24]#[N:25])=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:31][OH:32].CCN(C(C)C)C(C)C>C(O)C.C(OCC)(=O)C>[C:1]([C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:16][C:17](/[C:24](/[NH2:25])=[N:31]/[OH:32])=[C:18]([C:20]([F:22])([F:23])[F:21])[N:19]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 59128841HCID 59128841, compound

Product 1

HCID 136038633HCID 136038633, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-(2-(2-tert-butylphenoxy)pyridin-3-ylamino)-4-(trifluoromethyl)thiazole-5-carbonitrile (Example 404, 177 mg, 0.42 mmol), hydroxylamine hydrochloride salt (145 mg, 2.1 mmol), DIPEA (732 μL, 4.2 mmol) in ethanol (5 mL) was heated at 60° C. for 5 h. The reaction was diluted with ethyl acetate and washed with brine. The organic layer was separated and evaporated to give the crude product. Purification of the crude product by flash chromatography (silica, 0-80% EtOAc/hexane gradient) gave Example A53a (120 mg) as white crystals. (M+H)+=452.1.

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. customevaporated

Sources & evidence

ORD record
ord-fbe0bcf9d7b447e18da242deba6f6035
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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