4-Methylmorpholine → HCID 66786129, compound

HRID 1096637Notes

Reaction equation

HRID 1096637 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([C@@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20]C(C)(C)C)=O)[CH2:13]2)=O)=[C:5]([NH:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])[CH:4]=1.[C:31]([O:35][C:36]([NH:38][C@H:39]([CH2:44][C:45]1[CH:54]=[CH:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=1)[CH2:40]C(O)=O)=[O:37])([CH3:34])([CH3:33])[CH3:32].CN1C[CH2:60][O:59][CH2:58]C1.CN(C([O:69]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C:31]([O:35][C:36]([NH:38][C@H:39]([CH2:44][C:45]1[CH:54]=[CH:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=1)[CH2:40][C:18]([N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:10]2[N:25]([CH2:26][CH2:27][CH2:28][O:29][CH3:30])[C:5]3[C:4]([C:58]([O:59][CH3:60])=[O:69])=[CH:3][CH:8]=[CH:7][C:6]=3[N:9]=2)[CH2:13]1)=[O:20])=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 7021578(R)-3-((tert-butoxycarbonyl)amino)-4-(naphthalen-2-yl)butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66791505HCID 66791505, compound

Product 1

HCID 66786129HCID 66786129, compoundYield 16.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Methyl 1-(3-methoxypropyl)-2-(piperidin-3-yl)-1H-benzo[d]imidazole-7-carboxylate (42C) (0.36 mmol, 120 mg) in DMF (10 mL) was added (R)-3-(tert-butoxycarbonylamino)-4-(naphthalen-2-yl)butanoic acid (0.40 mmol, 132 mg) and N-methylmorpholine (1.44 mmol, 0.16 mL). The reaction mixture was stirred at rt for 5 min and then added HATU (0.40 mmol, 152 mg) and kept stirring at rt overnight. The reaction mixture was poured into H2O, extracted with EtOAc. The extract was washed with H2O, NaHCO3, brine, dried over MgSO4 and filtered. The filtrate was concentrated in vacuo and purified by preparative LC/MS (40-70% CH3CN in H2O) to afford methyl 2-(1-((R)-3-(tert-butoxycarbonylamino)-4-(naphthalen-2-yl)butanoyl)piperidin-3-yl)-1-(3-methoxypropyl)-1H-benzo[d]imidazole-7-carboxylate (44D) (0.06 mmol, 40 mg, yield: 16.7%). ESI-MS: m/z 643.5 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with H2O, NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by preparative LC/MS (40-70% CH3CN in H2O)

Sources & evidence

ORD record
ord-731d3347a1af405181ddd5535c669419
Source dataset
uspto-grants-2012_03
Patent number
US08138168B1

Reaction notes

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