Dimethylamine → HCID 69108521, compound

HRID 749030Notes

Reaction equation

HRID 749030 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:16][CH:15]=1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:33]([N:35](CC)[CH2:36]C)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CNC>C(Cl)Cl>[CH3:32][O:31][C:29](=[O:30])[CH2:28][CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[O:20][C:17]1[CH:18]=[CH:19][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:11])[N:35]([CH3:36])[CH3:33])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 69230869HCID 69230869, compound

Product 1

HCID 69108521HCID 69108521, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The hydrogenated compound 60 (2.2 g, 4.96 mmol) was dissolved in CH2Cl2 and stirred at room temperature under an atmosphere of argon. Triethylamine (0.829 mL, 5.95 mmol) and benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP reagent, 2.413 g, 5.456 mmol) were added and the reaction mixture was stirred for 15 min. Dimethylamine (2.0 M solution in THF, 12.4 mL, 24.8 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 (1×30 mL), water (2×50.0 mL) and brine (1×50.0 mL). Drying and concentration of the organic layer gave the desired amide crude (1.2 g, ˜98%). Flash chromatography on silica gel (methanol-chloroform 1%-2%) yielded the desired amide 75(0.8 g 98%) 1H NMR (400 MHz, DMSO-d6): 7.32 (dd, J=7.6 and 2 HZ, 1H), 7.21 (m, 3H), 7.08 (dd, J=14 and 7.2 Hz, 2H), 6.83 (d, J=8.8 Hz, 2H), 6.75 (d, J=8.0 Hz, 1H), 4.53 (m, 1H) 3.55 (s, 3H), 2.89 (s, 3H), 2.85-2.58 (m, 7H), 2.59 (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 (1×30 mL), water (2×50.0 mL) and brine (1×50.0 mL)
  5. customDrying

Sources & evidence

ORD record
ord-4655979183864bd8bd56b35532a7baf4
Source dataset
uspto-grants-2008_07
Patent number
US07399786B2

Reaction notes

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