Hydrochloric Acid → HCID 67466471, compound

HRID 1619955Notes

Reaction equation

HRID 1619955 reaction equation
[CH2:1]([CH:3]1[CH2:8][C:7](=[O:9])[NH:6][N:5]=[C:4]1[C:10]1[CH:32]=[CH:31][C:13]2[N:14]=[C:15]([C:17]3[CH:30]=[CH:29][C:20]([O:21][CH2:22][CH:23]4[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[O:16][C:12]=2[CH:11]=1)[CH3:2].Cl.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl.C(N(CC)CC)C>[CH2:1]([CH:3]1[C:4]([C:10]2[CH:32]=[CH:31][C:13]3[N:14]=[C:15]([C:17]4[CH:30]=[CH:29][C:20]([O:21][CH2:22][CH:23]5[CH2:24][CH2:25][N:26]([S:35]([CH3:34])(=[O:37])=[O:36])[CH2:27][CH2:28]5)=[CH:19][CH:18]=4)[O:16][C:12]=3[CH:11]=2)=[N:5][NH:6][C:7](=[O:9])[CH2:8]1)[CH3:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chloride2×HCID 67467152HCID 67467152, compound

Product 1

HCID 67466471HCID 67466471, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent2×

Procedure

15.5 mg (33 μmol) 4-{4-[6-(4-ethyl-6-oxo-1,4,5,6-tetrahydro-pyridazin-3-yl)-benzoxazol-2-yl]-phenoxymethyl}-piperidine as hydrochloride are stirred together with 2.6 μl (34 μmol) methanesulphonic acid chloride, 14 μl (100 μmol) triethylamine and 2 ml DCM at RT overnight within the next 4 days a further 14.4 μl methanesulphonic acid chloride and 24.5 μl triethylamine are added batchwise. Then the reaction mixture is combined with DCM and extracted 2× with 25 ml of water+3 drops of glacial acetic acid, 5% sodium carbonate solution and sat. saline solution. The solv. of the org. phase is evaporated off completely i.V. and the residue is stirred with cyclohexane/EA.

Workup

  1. additionare added batchwise
  2. extractionextracted 2× with 25 ml of water+3 drops of glacial acetic acid, 5% sodium carbonate solution and sat. saline solution
  3. customphase is evaporated off completely i.V

Sources & evidence

ORD record
ord-4fc38fb2b6414dbbafe65b7414a8f6d5
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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