Diethyl Ether → HCID 86616219, compound

HRID 1817847Notes

Reaction equation

HRID 1817847 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([Cl:9])=[O:8].CCN(C(C)C)C(C)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][C:22]=1[C:30]1[N:31]=[C:32]([NH:35][C:36]([C@H:38]2[CH2:43][CH2:42][CH2:41][NH:40][CH2:39]2)=[O:37])[S:33][CH:34]=1.C(OCC)C>C(#N)C.CCOC(C)=O.C(Cl)Cl>[ClH:9].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][C:22]=1[C:30]1[N:31]=[C:32]([NH:35][C:36]([C@H:38]2[CH2:43][CH2:42][CH2:41][N:40]([C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[O:8])[CH2:39]2)=[O:37])[S:33][CH:34]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 135034Pyridine-2-carbonyl chlorideHCID 86616221HCID 86616221, compound

Product 1

HCID 86616219HCID 86616219, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.071 g of picolinoyl chloride and then 0.12 mL of DIPEA are added, at a temperature of 0° C., to a solution of 0.12 g of the compound prepared in step 2.2, in 1 mL of acetonitrile. The medium is stirred until it has returned to room temperature. After 1 hour at room temperature, the medium is hydrolysed and then diluted with EtOAc and washed with 10% Na2CO3 solution and then with saturated NaCl solution. After drying over MgSO4, the solution is concentrated. The crude product obtained is taken up in DCM. The hydrochloride is formed by addition of 2 M hydrochloric ethyl ether. The solid obtained is filtered off and rinsed with ethyl ether. The free base is obtained by treatment with 1 M sodium hydroxide and is then extracted into DCM and the organic phase is dried over MgSO4 and then evaporated. The free base is taken up in DCM. The hydrochloride is obtained by addition of 2 M hydrochloric ethyl ether. The solid obtained is filtered off, rinsed with ethyl ether and then dried to give 91 mg of a white solid.

Workup

  1. customhas returned to room temperature
  2. washwashed with 10% Na2CO3 solution
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe solution is concentrated
  5. customThe crude product obtained

Sources & evidence

ORD record
ord-ac4579fb4046476cb4d1f6a413cd159c
Source dataset
uspto-grants-2009_10
Patent number
US07598392B2

Reaction notes

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