Dimethylamine → HCID 69113915, compound

HRID 749015Notes

Reaction equation

HRID 749015 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32]([N:34](CC)[CH2:35]C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.CNC>C(Cl)Cl>[CH3:31][O:30][C:28](=[O:29])[CH2:27][CH2:26][C:23]1[CH:24]=[CH:25][C:20]([C:17]2[CH:16]=[CH:15][C:14]([CH2:13][CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10](=[O:12])[N:34]([CH3:35])[CH3:32])=[CH:19][CH:18]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69113200HCID 69113200, compound

Product 1

HCID 69113915HCID 69113915, compoundYield 96.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The hydrogenated compound 44 (4.3 g, 10.0 mmol) was dissolved in CH2Cl2 (50 mL) and stirred at room temperature under an atmosphere of argon. Triethylamine (1.68 mL, 12.0 mmol) and BOP reagent (4.9 g, 11.0 mmol) were added and the reaction mixture was stirred for 15 min. Dimethylamine (2.0 M solution in THF, 25.0 mL, 50.0 mmol) was added and the resulting solution was stirred at room temperature for about 2-3 h. The solvent was removed under reduced pressure and the resulting oil was taken up in EtOAc (100 mL). The organic layer was extracted with 0.5 N NaOH (1×10 mL), water (2×50 mL) and brine (1×50 mL). Drying and concentration of the organic layer gave the desired amide 45 (4.4 g, 96%). 1H NMR (400 MHz, DMSO-d6): 7.56 (overlapped d, J=8.4 Hz, 2H), 7.55 (overlapped d, J=8.4 Hz, 2H), 7.32 (d, J=8.8 Hz, 2H), 7.30 (d, J=8.8 Hz, 2H), 7.13 (d, J=8.4 Hz, 1H), 4.58 (m, 1H), 3.60 (s, 3H), 2.94 (s, 3H), 2.89 (t, J=7.6 Hz, 2H), 2.79-2.83 (m, 5H), 2.67 (t, J=7.6 Hz, 2H), 1.31 (s, 9H).

Workup

  1. stirringthe reaction mixture was stirred for 15 min
  2. stirringthe resulting solution was stirred at room temperature for about 2-3 h
  3. customThe solvent was removed under reduced pressure
  4. extractionThe organic layer was extracted with 0.5 N NaOH (1×10 mL), water (2×50 mL) and brine (1×50 mL)
  5. customDrying

Sources & evidence

ORD record
ord-ba0b217d4c664075ad8e1b7211f39523
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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