Triethylamine → N1-[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]-N2-(3 4-dichlorophenyl)-N1,2-dimethylalaninamide

HRID 2354374Notes

Reaction equation

HRID 2354374 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([CH3:15])([C:12]([OH:14])=O)[CH3:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[Li].[C:17]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:22]=[CH:21][C:20]([CH:23]([NH:30][CH3:31])[CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1.C(N(CC)CC)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>CN(C=O)C>[C:17]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:22]=[CH:21][C:20]([CH:23]([N:30]([CH3:31])[C:12](=[O:14])[C:10]([CH3:11])([CH3:15])[NH:9][C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH2:24][N:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 27567161-([1,1'-Biphenyl]-4-yl)-N-methyl-2-(pyrrolidin-1-yl)ethan-1-amineHCID 3028194LithiumHCID 17605983HCID 17605983, compound

Product 1

HCID 59809575N1-[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]-N2-(3 4-dichlorophenyl)-N1,2-dimethylalaninamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3,4-dichlorophenyl)-2-methylalanine, lithium salt (100 mg, 0.4 mmol), [1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (124 mg, 0.44 mmol), triethylamine (246 uL, 1.77 mmol), and (1H-1,2,3-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (BOP Reagent, 215 mg, 0.486 mmol) were added in that order to a 4 mL screw capped vial that contained 2 mL of anhydrous DMF. The reaction mixture was stirred for 20 hours at room temperature, then filtered through a 0.45 um PTFE Acrodisk, and purified by reverse-phase HPLC (Xterra Prep RP C-18, 30×150 mm, 50 mL/min, A: acetonitrile B: water, pH 10 w/NH4OH, A: 20 to 99% over 9 min, UV detection at 214 nm) to give the title compound as a white solid. MS (ES) m/e 510 [M+H]+.

Workup

  1. customcapped vial
  2. filtrationfiltered through a 0.45 um PTFE Acrodisk
  3. custompurified by reverse-phase HPLC (Xterra Prep RP C-18, 30×150 mm, 50 mL/min
  4. waitA: 20 to 99% over 9 min

Sources & evidence

ORD record
ord-1551f818669e4d539288c1d9da874f15
Source dataset
uspto-grants-2010_07
Patent number
US07749998B2

Reaction notes

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