Triethylamine → HCID 178505143, compound

HRID 1260728Notes

Reaction equation

HRID 1260728 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)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37].[OH-].[Na+]>ClCCl>[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][S:36]([CH3:35])(=[O:38])=[O:37])[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

6

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 31297Methanesulfonyl chlorideHCID 178478590HCID 178478590, compound2×

Product 1

HCID 178505143HCID 178505143, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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) (70.4 mg, 0.16 mmol) in dichloromethane (1 ml) was added at room temperature triethylamine (89 mg, 123 μl, 880 μmol) and methanesulfonyl chloride (27.5 mg, 18.7 μl, 240 μmol). The mixture was allowed to stir at room temperature for 18 h, poured into ice/water (5 ml) and 1N sodium hydroxide solution (5 ml) and extracted with dichloromethane (2×15 ml). The combined organic layers were washed with brine (15 ml), dried (MgSO4) and evaporated. The crude material was further purified by flash chromatography on silica gel (dichloromethane/MeOH 9:1) and trituration with dichloromethane (1 ml) and heptane (5 mL) for 30 min to yield the title compound as an off-white solid (43 mg, 66%), MS (ISP) m/z=409.4 [(M+H)+], mp 220° C.

Workup

  1. extractionextracted with dichloromethane (2×15 ml)
  2. washThe combined organic layers were washed with brine (15 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe crude material was further purified by flash chromatography on silica gel (dichloromethane/MeOH 9:1) and trituration with dichloromethane (1 ml) and heptane (5 mL) for 30 min

Sources & evidence

ORD record
ord-01424643e4ce4769bc28ab938e830b62
Source dataset
uspto-grants-2013_06
Patent number
US08470828B2

Reaction notes

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