Azepane → HCID 59542474, compound

HRID 1809094Notes

Reaction equation

HRID 1809094 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:15][CH:16]=[C:17]([C:19]([OH:21])=O)[CH:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:53]1[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:53]3[CH2:59][CH2:58][CH2:57][CH2:56][CH2:55][CH2:54]3)=[O:21])[CH:18]=2)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8119AzepaneHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59542569HCID 59542569, compound

Product 1

HCID 59542474HCID 59542474, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-Carboxy-thiophen-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (0.075 g, 0.24 mmol) was dissolved in DMF (2 mL). Triethylamine (0.72 mmol), HATU (0.26 mmol) and homopiperidine (0.26 mmol) were added and the reaction stirred at room temperature overnight. The reaction mixture was purified directly by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.066 g). LCMS m/z 393.26 [M+H]+ RT=4.05 min (Analytical Method 4).

Workup

  1. customThe reaction mixture was purified directly by HPLC
  2. washeluting with 10%-98% acetonitrile in water (0.1% formic acid) over 30 minutes
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-95a6948465794665ad742dc75919db7d
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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