Fumaric Acid → (cis)-6-(3-Pyridinyl)-3,6-diazabicyclo[3.2.0]heptane fumarate

HRID 1817002Notes

Reaction equation

HRID 1817002 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][CH:12]3[CH:8]2[CH2:9][NH:10][CH2:11]3)[CH:2]=1.[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18]>CO.C(OC(=O)C)(C)C>[C:14]([OH:21])(=[O:20])/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:13][C@@H:12]3[C@H:8]2[CH2:9][NH:10][CH2:11]3)[CH:2]=1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 98128976-(3-Pyridinyl)-3,6-diazabicyclo[3,2,0]heptane

Product 1

HCID 23636030(cis)-6-(3-Pyridinyl)-3,6-diazabicyclo[3.2.0]heptane fumarateYield 44%

Reagents, catalysts & solvents 1

HCID 22498805Methanol isopropylacetateSolvent

Procedure

The product of Example 40C (65 mg, 0.37 mmol) was treated with fumaric acid (46.4 mg, 0.4 mmol) in methanol/isopropylacetate (1:10 v/v, 20 mL). The mixture was stirred at room temperature overnight. The precipitate was collected by filtration and dried under reduced pressure at 40-50° C. to provide the title compound (47 mg, 44% yield). 1H NMR (MeOH-d4, 300 MHz) δ 3.18 (dd, J=12.6, 3.4 Hz, 1H), 3.35 (m, 1H), 3.46 (m, 1H), 3.75 (m, 3H), 4.04 (t, J=7.5 Hz, 1H), 4.90 (m, 1H), 6.58 (s, 2H), 7.04 (ddd, J=8.2, 2.7, 1.3 Hz, 1H), 7.27 (dd, J=8.2, 4.8 Hz, 1H), 7.87 (d, 2.7 Hz, 1H), 7.95 (dd, J=4.8, 1.1 Hz, 1H); m/z 176 (M+H)+; Anal. calculated for C10H13N3.1.25C4H4O4.0.6H2O: C, 54.41; H, 5.84; N, 12.69. Found: C, 54.96; H, 5.50; N, 12.10.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried under reduced pressure at 40-50° C.

Sources & evidence

ORD record
ord-206e20d2faee41e384019e9d8ac1de56
Source dataset
uspto-grants-2009_10
Patent number
US07598236B2

Reaction notes

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