Triethylamine → HCID 44561157, compound

HRID 2114329Notes

Reaction equation

HRID 2114329 reaction equation
[C:1]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=[CH:5][C:4]([CH:7]([NH:14][CH3:15])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:30]([CH3:35])[CH2:31][C:32]([OH:34])=O)[CH:26]=[CH:27][C:28]=1[Cl:29].C(N(CC)CC)C>ClCCl>[C:1]1([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:6]=[CH:5][C:4]([CH:7]([N:14]([CH3:15])[C:32](=[O:34])[CH2:31][N:30]([C:25]2[CH:26]=[CH:27][C:28]([Cl:29])=[C:23]([Cl:22])[CH:24]=2)[CH3:35])[CH2:8][N:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27567161-([1,1'-Biphenyl]-4-yl)-N-methyl-2-(pyrrolidin-1-yl)ethan-1-amineHCID 57418650N-(3,4-dichlorophenyl)-N-methylglycine

Product 1

HCID 44561157HCID 44561157, compoundYield 58.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(4-biphenylyl)-2-(1-pyrrolidinyl)ethyl]methylamine (50 mg, 0.18 mmol) was added to a solution of N-(3,4-dichlorophenyl)-N-methylglycine (49 mg, 0.21 mmol), (benzotriazol-1-yloxy) tris(dimethylamino) phosphonium-hexaflurophosphate (BOP) (118 mg, 0.27 mmol) and triethylamine (TEA) (54 mg, 0.54 mmol) in dichloromethane (DCM) (2.0 mL), The reaction mixture was stirred at room temperature for 3 h and was then concentrated in vacuo. To the residue was added 4 mL of saturated solution of Na2CO3 and then extracted by ethyl acetate (2×3 mL). The combined organic layers were concentrated in vacuo to give a brown solid, which was purified by using a Gilson preparative HPLC system (Phenomenex 75×30 mm column, 40 mL/min flow rate, A: 0.1% TFA in acetonitrile B: 0.1% TFA in water, A: 10 to 100% over 15 min, UV detection at 215 nm) to yield the title compound (52 mg, 58%). MS (ES) m/e 496 [M+H]+.

Workup

  1. concentrationwas then concentrated in vacuo
  2. additionTo the residue was added 4 mL of saturated solution of Na2CO3
  3. extractionextracted by ethyl acetate (2×3 mL)
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customto give a brown solid, which
  6. customwas purified
  7. waitA: 0.1% TFA in acetonitrile B: 0.1% TFA in water, A: 10 to 100% over 15 min

Sources & evidence

ORD record
ord-ffacb749cf924751afffb9b87318792f
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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