Oxalic Acid → 5-Chloro-7-{5-[1-(tetrahydro pyran-4-yl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-2,3-dihydro benzofuran-4-ylamine oxalate salt

HRID 1523737Notes

Reaction equation

HRID 1523737 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH2:19][CH2:18]3)=[N:15][N:16]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[NH2:11].[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31]>C(O)C.CC(O)C>[C:29]([OH:34])(=[O:33])[C:30]([OH:32])=[O:31].[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:13][C:14]([CH:17]3[CH2:18][CH2:19][N:20]([CH:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)[CH2:21][CH2:22]3)=[N:15][N:16]=2)[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[C:10]=1[NH2:11]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 715347815-Chloro-7-{5-[1-(tetrahydro pyran-4-yl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-2,3-dihydro benzofuran-4-yl amine

Product 1

HCID 715347805-Chloro-7-{5-[1-(tetrahydro pyran-4-yl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-2,3-dihydro benzofuran-4-ylamine oxalate saltYield 90.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 5-chloro-7-{5-[1-(tetrahydro pyran-4-yl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-2,3-dihydro benzofuran-4-ylamine (20.4 mg, 0.05 mmol) in ethanol (2 mL), oxalic acid (6.0 mg, 0.05 mmol) was added. After stirring at room temperature for 1 hour the reaction was further diluted with 2-propanol and refluxed for 2 hour; The volatiles were removed under reduced pressure and the crude product obtained was triturated with ether, dried under vacuum to obtain 5-chloro-7-{5-[1-(tetrahydro pyran-4-yl) piperidin-4-yl]-[1,3,4]oxadiazol-2-yl}-2,3-dihydro benzofuran-4-ylamine oxalate salt (22.5 mg).

Workup

  1. temperaturerefluxed for 2 hour
  2. customThe volatiles were removed under reduced pressure
  3. customthe crude product obtained
  4. customwas triturated with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-01a40d0ffa0e42b084f94fd63c36b44f
Source dataset
uspto-grants-2015_07
Patent number
US09079894B2

Reaction notes

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