Dichloromethane → Azepan-1-yl-(5-pyridin-4-yl-thiophen-3-yl)-methanone

HRID 2068617Notes

Reaction equation

HRID 2068617 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)=[CH:3][CH:2]=1.[N:15]1([C:22](=O)[CH3:23])[CH2:21][CH2:20][CH2:19]NCC1.[CH3:25]N(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)Cl>CC#N>[N:15]1([C:12]([C:9]2[CH:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[S:11][CH:10]=2)=[O:14])[CH2:21][CH2:20][CH2:19][CH2:25][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 4186202N-AcetylhomopiperazineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 581102285-Pyridin-4-yl-thiophene-3-carboxylic acid

Product 1

HCID 44224462Azepan-1-yl-(5-pyridin-4-yl-thiophen-3-yl)-methanoneYield 28.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Pyridin-4-yl-thiophene-3-carboxylic acid (0.4 mmol) was dissolved in MeCN (2 mL). 1-[1,4]Diazepan-1-yl-ethanone (1.8 mmol), and HATU (0.4 mmol) were added and the reaction mixture stirred for 72 hours. DCM (20 mL) was added and the organic solution was separated and the solvent removed by evaporation. The residue was purified by HPLC, eluting with 10%-90% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound as a white solid (33 mg). LCMS m/z 287.09 [M+H]+ RT=5.20 min. (Analytical Method 2). 1H NMR (400 MHz, MeCN-d): δ 8.6 (d, 2H), 7.95 (d, 2H), 7.9 (s, 1H), 7.8 (s, 1H), 3.6 (t, 2H), 3.5 (t, 2H), 1.8-1.6 (m, 6H).

Workup

  1. customthe organic solution was separated
  2. customthe solvent removed by evaporation
  3. customThe residue was purified by HPLC
  4. washeluting with 10%-90% acetonitrile in water (0.1% formic acid) over 30 minutes
  5. additionThe fractions containing the desired product
  6. concentrationwere concentrated under vacuum
  7. customfreeze-dried

Sources & evidence

ORD record
ord-b52d0a806f1649aea43a78bb72a5acf5
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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