4-Methylmorpholine → HCID 24760562, compound

HRID 639531Notes

Reaction equation

HRID 639531 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:20]([F:22])[F:21])[CH:14]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:56]1[C:60]2=[C:61]([C:65](O)=[O:66])[N:62]=[CH:63][CH:64]=[C:59]2[CH:58]=[CH:57]1>CN(C=O)C>[C:1]([C:5]1[CH:24]=[CH:23][C:8]([CH2:9][N:10]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH:20]([F:22])[F:21])[CH:14]=2)[C:65]([C:61]2[N:62]=[CH:63][CH:64]=[C:59]3[CH:58]=[CH:57][NH:56][C:60]=23)=[O:66])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 534130241H-Pyrrolo[2,3-c]pyridine-7-carboxylic acidHCID 68576819(4-Tert-butyl-benzyl)-[2-(3-difluoromethoxy-phenyl)-ethyl]-amine

Product 1

HCID 24760562HCID 24760562, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(4-tert-Butyl-benzyl)-[2-(3-difluoromethoxy-phenyl)-ethyl]-amine (90 mg, 0.27 mmol), N-methylmorpholine (74 mg, 0.73 mmol), and HBTU (139 mg, 0.37 mmol) were added at RT to a solution of 1H-pyrrolo[2,3-c]pyridine-7-carboxylic acid (66 mg) in DMF (3 mL), then after 64 h the reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography of the residue (SiO2, heptane-dichloromethane gradient) afforded the title compound (108 mg, 86% over 2 steps). Light yellow oil, MS (ISP) 478.4 (M+H)+.

Workup

  1. customafter 64 h the reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-bf4b9533beae474b9d7725785bc78210
Source dataset
uspto-grants-2010_04
Patent number
US07691876B2

Reaction notes

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