Azepane → HCID 42646245, compound

HRID 1809092Notes

Reaction equation

HRID 1809092 reaction equation
[CH:1]1([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>C(#N)C>[N:46]1([C:12]([C:9]2[CH:8]=[C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[S:11][CH:10]=2)=[O:14])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

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 5954250313191-44-1

Product 1

HCID 42646245HCID 42646245, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(Cyclohexyl)-thiophene-3-carboxylic acid (0.03 g, 0.14 mmol) was dissolved in acetonitrile (2 mL). Triethylamine (0.42 mmol), HATU (0.15 mmol) and azepane (0.14 mmol) were added and the reaction stirred at room temperature overnight. The resulting solution 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 (0.022 g). LCMS m/z 292.22 [M+H]+ RT=13.57 min (Analytical Method 1). 1H NMR δ (ppm) (CHCl3-d): 7.2 (s, 1H), 6.95 (s, 1H), 3.7-3.4 (m, 4H), 2.8 (m, 1H), 2.1 (m, 2H), 1.9-1.2 (m, 16H).

Workup

  1. customThe resulting solution 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-09c0d99a1d314cf49cac836cb38a62e3
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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