Triethylamine → HCID 44227299, compound

HRID 2068618Notes

Reaction equation

HRID 2068618 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.Cl.[CH3:11][C:12]1([CH3:19])[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C.O>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([N:15]2[CH2:16][CH2:17][CH2:18][C:12]([CH3:19])([CH3:11])[CH2:13][CH2:14]2)=[O:9])[CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 120399785-Bromothiophene-3-carboxylic acidHCID 66850259HCID 66850259, compound

Product 1

HCID 44227299HCID 44227299, compoundYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5-Bromo-thiophene-3-carboxylic acid (0.5 g, 2.42 mmol), 4,4-dimethyl-azepane hydrochloride (0.475 g, 2.91 mmol), triethylamine (1.01 mL, 7.25 mmol) and HATU (1.20 g, 3.16 mmol) were dissolved in acetonitrile (10 mL) and the resulting mixture stirred overnight. The mixture was diluted with water and extracted with DCM (×2). The organics were dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on a silica II cartridge, eluting with 10-25% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give (5-bromo-thiophen-3-yl)-(4,4-dimethyl-azepan-1-yl)methanone (0.55 g).

Workup

  1. extractionextracted with DCM (×2)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by chromatography on a silica II cartridge
  6. washeluting with 10-25% ethyl acetate in cyclohexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-76a6553d232642c7949951542281c46e
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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