Hydrochloric Acid → HCID 21963938, compound

HRID 2212386Notes

Reaction equation

HRID 2212386 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[O:21][CH:22]=[CH:23][C:24]=3[CH:25]=O)=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1.C([BH3-])#N.[Na+].Cl>CO.C(OCC)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2([C:27]3[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:28]=3[F:34])[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([C:20]3[O:21][CH:22]=[CH:23][C:24]=3[CH2:25][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[O:19])[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 21963945HCID 21963945, compound

Product 1

HCID 21963938HCID 21963938, compoundYield 22.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of the product of Example 143 (100 mg, 0.19 mmol) in methanol (2.5 mL) was added morpholine (100 μL, 1.7 mmol) and sodium cyanoborohydride (9 mg, 0.19 mmol) followed by hydrochloric acid (3M solution in methanol, 0.3 mL) dropwise. The reaction was stirred at room temperature for 20 hours then diluted with diethyl ether and 4N aqueous sodium hydroxide. The organic layer was washed with water, dried (MgSO4) and evaporated to dryness, yielding a yellow oil which was purified by column chromatography on silica eluting with 1:1:1 iso-hexane:dichloromethane:ethyl acetate +1% triethylamine to yield the desired product as a white solid (25 mg).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness
  4. customyielding a yellow oil which
  5. customwas purified by column chromatography on silica eluting with 1:1:1 iso-hexane

Sources & evidence

ORD record
ord-7f7afdb9c46e4026b72fc272e6dc82cb
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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