Diisopropylethylamine → HCID 117761045, compound

HRID 523262Notes

Reaction equation

HRID 523262 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[S:10]1[CH:14]=[CH:13][N:12]=[C:11]1[CH2:15][C:16](O)=[O:17].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:16](=[O:17])[CH2:15][C:11]2[S:10][CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 1235383-Bromo-o-toluidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 212206632-Thiazoleacetic acid

Product 1

HCID 117761045HCID 117761045, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-bromo-2-methylaniline (0.764 mL, 6.20 mmol), 1,3-thiazol-2-ylacetic acid (0.74 g, 5.17 mmol) and DIEA (1.63 mL, 9.30 mmol) in DMF (15 mL) was treated with HATU (2.36 g, 6.20 mmol). After stirring overnight, the mixture was diluted with EtOAc, washed twice with 10% aqueous LiCl followed by brine, and the combined aqueous layers were extracted with EtOAc. The combined organic layers were dried and concentrated, and the residue was purified by column chromatography on silica gel, eluting with EtOAc-hexanes, to give N-(3-bromo-2-methylphenyl)-2-(thiazol-2-yl)acetamide as a white solid (0.681 g, 42% yield). 1H NMR (400 MHz, chloroform-d) δ 9.84-9.65 (m, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.84 (d, J=3.3 Hz, 1H), 7.42-7.35 (m, 2H), 7.07 (t, J=8.0 Hz, 1H), 4.18 (s, 2H), 2.38 (s, 3H).

Workup

  1. washwashed twice with 10% aqueous LiCl
  2. extractionthe combined aqueous layers were extracted with EtOAc
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customthe residue was purified by column chromatography on silica gel
  6. washeluting with EtOAc-hexanes

Sources & evidence

ORD record
ord-797cbe1dd4a54a20937e61a4826ab618
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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