Morpholine → HCID 24955984, compound

HRID 607421Notes

Reaction equation

HRID 607421 reaction equation
[CH3:1][S:2]([C:30]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][C:38](O)=[O:39])=[CH:32][CH:31]=1)(=[N:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[C:11]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][C:22]([C:24]3[O:25][CH:26]=[CH:27][C:28]=3[CH3:29])=[O:23])[CH:16]=2)[CH:12]=1)=[O:6])=[O:3].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[NH:68]1[CH2:73][CH2:72][O:71][CH2:70][CH2:69]1>CN(C=O)C.CCOC(C)=O>[CH3:29][C:28]1[CH:27]=[CH:26][O:25][C:24]=1[C:22]([NH:21][C:17]1[CH:16]=[C:15]([C:14]#[C:13][C:11]2[CH:10]=[N:9][CH:8]=[C:7]([CH:12]=2)[C:5]([N:4]=[S:2]([CH3:1])([C:30]2[CH:31]=[CH:32][C:33]([CH2:36][CH2:37][C:38]([N:68]3[CH2:73][CH2:72][O:71][CH2:70][CH2:69]3)=[O:39])=[CH:34][CH:35]=2)=[O:3])=[O:6])[CH:20]=[CH:19][CH:18]=1)=[O:23]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 24955983HCID 24955983, compound

Product 1

HCID 24955984HCID 24955984, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[4-(S-methyl-N-{[5-({3-[(3-methyl-2-furoyl)amino]phenyl}-ethynyl)pyridin-3-yl]carbonyl}sulfonimidoyl)phenyl]propanoic acid (0.050 g, 0.090 mmol) was dissolved in DMF (1 mL) then treated with BOP (0.051 g, 0.117 mmol) and TEA (0.050 mL, 0.360 mmol) and allowed to stir for 20 min. Morpholine (0.015 mL, 0.180 mmol) was then added and the reaction was allowed to stir for an additional 4 h. The resulting reaction mixture was dissolved in EtOAc (5 mL) and then extracted with brine (2×5 mL). The organic layer was then dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude mixture was then purified via column chromatography (silica gel, gradient eluant mixture of MeOH in EtOAc: 0% to 0% MeOH) give the title compound (0.023 g, 41%).

Workup

  1. stirringto stir for an additional 4 h
  2. customThe resulting reaction mixture
  3. extractionextracted with brine (2×5 mL)
  4. dry with materialThe organic layer was then dried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture was then purified via column chromatography (silica gel, gradient eluant mixture of MeOH in EtOAc: 0% to 0% MeOH)

Sources & evidence

ORD record
ord-cf102901e74946eba46a794ef777c5a1
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Reaction notes

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