Azepane → HCID 42644590, compound

HRID 1809057Notes

Reaction equation

HRID 1809057 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][CH:19]=[C:20]([C:22](O)=[O:23])[CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.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.[NH:58]1[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([N:58]3[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60][CH2:59]3)=[O:23])[CH:21]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8119AzepaneHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59542554HCID 59542554, compound

Product 1

HCID 42644590HCID 42644590, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-Carboxy-thiophen-2-yl)-piperidine-1-carboxylic acid benzyl ester (0.095 g, 0.27 mmol) was dissolved in DMF (2 mL). DIPEA (0.54 mmol), HATU (0.27 mmol) and homopiperidine (0.27 mmol) were added and the reaction stirred at room temperature for 1 hour. The reaction mixture was partitioned between ethyl acetate and water. The organic solution was separated and dried with magnesium sulphate, filtered and the solvent removed under vacuum. The residue was purified by HPLC, eluting with 40%-90% 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 (0.032 g). LCMS m/z 427.29 [M+H]+ RT=12.22 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 7.4-7.35 (m, 4H), 7.35-7.3 (m, 1H), 7.25 (s, 1H), 6.9 (s, 1H), 5.15 (s, 2H), 4.3 (m, 2H), 3.6 (m, 2H), 3.5 (m, 2H), 3.00-2.90 (m, 3H), 2.0 (m, 2H), 1.8 (m, 2H), 1.75-1.5 (m, 8H).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic solution was separated
  3. dry with materialdried with magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent removed under vacuum
  6. customThe residue was purified by HPLC
  7. washeluting with 40%-90% acetonitrile in water (0.1% formic acid) over 30 minutes
  8. additionThe fractions containing the desired product
  9. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-a2fea5a6315642e99e59e21d351dd597
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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