Acetic Acid → HCID 178474976, compound

HRID 1260709Notes

Reaction equation

HRID 1260709 reaction equation
Cl.Cl.Cl.[O:4]1[C:8]2=[C:9]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[N:10]=[CH:11][CH:12]=[C:7]2[CH2:6][CH2:5]1.C(N(CC)C(C)C)(C)C.[C:37](O)(=[O:39])[CH3:38].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[OH-].[Na+]>CN(C=O)C>[O:4]1[C:8]2=[C:9]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH:27][C:37](=[O:39])[CH3:38])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[N:10]=[CH:11][CH:12]=[C:7]2[CH2:6][CH2:5]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178478590HCID 178478590, compound2×

Product 1

HCID 178474976HCID 178474976, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of trans-4-{2-[4-(2,3-dihydro-furo[2,3-c]pyridin-7-yl)-piperazin-1-yl]-ethyl}-cyclohexylamine trihydrochloride (intermediate B) (132 mg, 0.3 mmol) in DMF (2.2 ml) was added N,N-diisopropylethylamine (252 mg, 334 μl, 1.95 mmol), acetic acid (21.6 mg, 20.6 μl, 360 μmol) and TBTU (154 mg, 480 μmol). The mixture was allowed to stir at room temperature for 4 h, poured into ice/water (5 ml) and 1N NaOH (5 ml) and extracted with dichloromethane/MeOH (9:1, 20 ml). The organic phase was washed with brine (20 ml), dried (MgSO4) and evaporated. The crude material (0.13 g) was triturated with dichloromethane (1 ml) and heptane (5 ml) for 30 min, the precipitate was collected by filtration, washed with heptane and dried to yield the title compound as a white solid (95 mg, 85%), MS (ISP) m/z=372.9 [(M+H)+], mp 195° C.

Workup

  1. extractionextracted with dichloromethane/MeOH (9:1, 20 ml)
  2. washThe organic phase was washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude material (0.13 g) was triturated with dichloromethane (1 ml) and heptane (5 ml) for 30 min
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with heptane
  8. customdried

Sources & evidence

ORD record
ord-5ba9a04f059b4e44adcb80113b62d858
Source dataset
uspto-grants-2013_06
Patent number
US08470828B2

Reaction notes

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