2,6-Dimethylmorpholine, cis- → HCID 86662644, compound

HRID 38865Notes

Reaction equation

HRID 38865 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.[CH3:39][C@H:40]1[O:45][C@@H:44]([CH3:46])[CH2:43][NH:42][CH2:41]1>>[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:42]4[CH2:41][C@H:40]([CH3:39])[O:45][C@H:44]([CH3:46])[CH2:43]4)=[N:35][N:36]=3)[CH:14]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 6415002,6-Dimethylmorpholine, cis-HCID 86662638HCID 86662638, compound

Product 1

HCID 86662644HCID 86662644, compoundYield 27.6%

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 (50 mg, 0.084 mmol) and (2R,6S)-2,6-dimethylmorpholine (0.5 ml, 0.084 mmol) were placed a vial and heated in a microwave at 90° C. for 15 mins. The reaction was heated in the microwave for a further 20 mins. The (2R,6S)-2,6-dimethylmorpholine was removed and the residue placed into isopropanol (3 ml) and 2M sodium hydroxide (1 ml) and the mixture stirred at room temperature for 3 h. The solvent was removed and the residue purified by Mass Directed Automated Preparative HPLC (Method B). The desired product was not collected so the waste was concentrated in vacuo and the residue purified by Mass Directed Automated Preparative HPLC (Method B) to give the title compound as white solid (12 mg).

Workup

  1. temperatureThe reaction was heated in the microwave for a further 20 mins
  2. customThe (2R,6S)-2,6-dimethylmorpholine was removed
  3. customThe solvent was removed
  4. customthe residue purified by Mass Directed Automated Preparative HPLC (Method B)
  5. customThe desired product was not collected so the waste
  6. concentrationwas concentrated in vacuo
  7. customthe residue purified by Mass Directed Automated Preparative HPLC (Method B)

Sources & evidence

ORD record
ord-41128cd80b9f4d918ca1c43edf31c1e4
Source dataset
uspto-grants-2013_09
Patent number
US08524751B2

Reaction notes

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