Morpholine → HCID 11717388, compound

HRID 2354990Notes

Reaction equation

HRID 2354990 reaction equation
Cl.Cl.[CH2:3]([N:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21](O)=[O:22])=[CH:15]3)[CH2:7][CH2:6]1)[CH3:4].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[NH:55]1[CH2:60][CH2:59][O:58][CH2:57][CH2:56]1>CN(C=O)C>[CH2:3]([N:5]1[CH2:6][CH2:7][CH:8]([NH:11][C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[NH:17][C:16]([C:21]([N:55]2[CH2:60][CH2:59][O:58][CH2:57][CH2:56]2)=[O:22])=[CH:15]3)[CH2:9][CH2:10]1)[CH3:4]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 131727197HCID 131727197, compound2×

Product 1

HCID 11717388HCID 11717388, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.15 g 5-(1-ethyl-piperidin-4-ylamino)-1H-indole-2-carboxylic acid (intermediate 3), 0.16 g O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (TBTU), 0.323 g DIPEA and 0.044 g morpholine in 2 ml DMF was reacted for 1 h at room temperature and evaporated to dryness. The residue was treated with ethyl acetate, water and NaHCO3 aq. The aqueous phases were further extracted with ethyl acetate and the combined organic phases were dried over Na2SO4, filtered and evaporated. The residue was further purified by chromatography and crystallization to yield 0.09 g (60%) of the title compound as light brown solid. MS (m/e): 357.4 (MH+, 100%).

Workup

  1. customwas reacted for 1 h at room temperature
  2. customevaporated to dryness
  3. additionThe residue was treated with ethyl acetate, water and NaHCO3 aq. The aqueous phases
  4. extractionwere further extracted with ethyl acetate
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was further purified by chromatography and crystallization

Sources & evidence

ORD record
ord-9bbd038283fd403da7f01624b1e93737
Source dataset
uspto-grants-2010_07
Patent number
US07754736B2

Reaction notes

Loading…