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4-Methylmorpholine → Ammonium Hydroxide

HRID 379047
Notes
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Reaction equation

HRID 379047 reaction equation
Cl.Cl.[NH2:3]C[C:5]1[N:9]([CH2:10][C:11]2[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:19])[CH:12]=2)[CH:8]=[N:7][CH:6]=1.[CH:20]1([CH2:26][C:27]([OH:29])=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[CH3:30][N:31]([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[C:15]([C:14]1[CH:17]=[CH:18][C:11]([CH2:10][N:9]2[CH:5]=[CH:6][N:7]=[C:8]2[CH2:30][NH:31][C:27](=[O:29])[CH2:26][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:12][C:13]=1[F:19])#[N:16].[NH4+:3].[OH-:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 21363Cyclohexaneacetic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 21697017HCID 21697017, compound

Product 2

HCID 14923Ammonium HydroxideHCID 21697089HCID 21697089, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(5-aminomethyl-imidazol-1-ylmethyl)-2-fluoro-benzonitrile dihydrochloride (0.17 g, 0.651 mmol) in DMF (5.0 mL) was added cyclohexylacetic acid (0.11 g, 0.782 mmol), BOP reagent (0.433 g, 0.977 mmol), and NMM (0.28 mL, 2.6 mmol). The mixture was stirred for 18 hr. The DMF was removed in vacuo and the residue was partitioned with EtOAc and saturated NaHCO3 solution. The EtOAc layer was washed with H2O, brine, and dried (MgSO4). Filtration and concentration in vacuo gave the title compound after chromatography (silica gel, CH2Cl2:CH3OH:NH4OH/97:3:0.3).

Workup

  1. customThe DMF was removed in vacuo
  2. customthe residue was partitioned with EtOAc and saturated NaHCO3 solution
  3. washThe EtOAc layer was washed with H2O, brine
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration in vacuo

Sources & evidence

ORD record
ord-f9505d32838e41ee8142074152ce943c
Source dataset
uspto-grants-2001_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06297239B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes