4-Methylmorpholine → HCID 178427131, compound

HRID 2053770Notes

Reaction equation

HRID 2053770 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1.[Cl:47][C:48]1[CH:65]=[CH:64][C:51]2[NH:52][C:53]([C@@H:55]([NH2:63])[CH2:56][C:57]3[CH:62]=[CH:61][N:60]=[CH:59][CH:58]=3)=[N:54][C:50]=2[CH:49]=1>CN(C)C=O>[Cl:47][C:48]1[CH:65]=[CH:64][C:51]2[NH:52][C:53]([C@@H:55]([NH:63][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([C:11]([N:13]4[CH2:17][CH2:16][CH2:15][CH2:14]4)=[O:12])=[C:2]([CH3:1])[CH:3]=3)[CH2:56][C:57]3[CH:58]=[CH:59][N:60]=[CH:61][CH:62]=3)=[N:54][C:50]=2[CH:49]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 120686863-Methyl 4-(pyrrolidin-1-ylcarbonyl)benzoic acidHCID 178511777HCID 178511777, compound

Product 1

HCID 178427131HCID 178427131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.150 g (0.579 mmol) of 3-methyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid, 0.186 g (0.579 mmol) of TBTU, and 0.20 mL (1.78 mmol) of N-methylmorpholine in 2 mL of N,N-dimethylformamide is stirred for 10 minutes at ambient temperature and then combined with a solution of 0.158 g (0.579 mmol) of (S)-1-(5-chloro-1H-benzimidazol-2-yl)-2-pyridin-4-ylethylamine. The reaction mixture is stirred for one day at ambient temperature, then poured onto ice water and extracted three times with ethyl acetate. The combined organic phases are dried with sodium sulfate and concentrated. The residue is chromatographed on silica gel, eluting with dichloromethane/methanol (95:10). Yield: 61.5 mg (22% of theory); Rf value: 0.44 (silica gel; dichloromethane/methanol=9:1); C27H26ClN5O2 (487.99); mass spectrum: (M−H)−=486/488 (chlorine isotope).

Workup

  1. additionpoured onto ice water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases are dried with sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel
  6. washeluting with dichloromethane/methanol (95:10)

Sources & evidence

ORD record
ord-94a1a477bad740d7b3e67091e0babecf
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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