Morpholine → HCID 86662645, compound

HRID 38866Notes

Reaction equation

HRID 38866 reaction equation
[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][N:19]3S(C3C=CC(C)=CC=3)(=O)=O)=[C:15]([C:32]3[O:33][C:34]([CH2:37]Cl)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.[OH-].[Na+]>C(O)(C)C>[Cl:1][C:2]1[C:7]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])=[CH:6][C:5]([C:13]2[CH:21]=[C:20]3[C:16]([CH:17]=[N:18][NH:19]3)=[C:15]([C:32]3[O:33][C:34]([CH2:37][N:39]4[CH2:44][CH2:43][O:42][CH2:41][CH2:40]4)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8083Morpholine2×HCID 14798Sodium HydroxideHCID 86662638HCID 86662638, compound

Product 1

HCID 86662645HCID 86662645, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

N-(2-Chloro-5-{4-[5-(chloromethyl)-1,3,4-oxadiazol-2-yl]-1-[(4-methylphenyl)sulfonyl]-1H-indazol-6-yl}-3-pyridinyl)methanesulfonamide (30 mg, 0.051 mmol) and morpholine (1 ml, 11.48 mmol) were placed a vial and heated in a microwave at 90° C. for 15 mins. The morpholine was blown off under a stream of nitrogen and the residue suspended in isopropanol (2 ml) and 2M sodium hydroxide (1 ml) added. The mixture was stirred at room temperature for 2 h. The solvent was blown off and the residue purified by chromatography on a silica gel (20 g) cartridge, eluting with 0-25% methanol in dichloromethane over 30 mins. The solvent was removed in vacuo and the residue loaded onto a SCX (10 g) cartridge and eluted with methanol and then 2M ammonia in methanol. The residue was purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound as a white solid (5 mg).

Workup

  1. customthe residue purified by chromatography on a silica gel (20 g) cartridge
  2. washeluting with 0-25% methanol in dichloromethane over 30 mins
  3. customThe solvent was removed in vacuo
  4. washeluted with methanol
  5. customThe residue was purified by Mass Directed Automated Preparative HPLC (Method B)

Sources & evidence

ORD record
ord-c44073ca31d642fea096e3af03bc25f5
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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