Triethylamine → HCID 57980075, compound

HRID 1677153Notes

Reaction equation

HRID 1677153 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH:19]1[CH2:23][CH2:22][CH2:21][C@H:20]1[CH2:24][N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1.C(N(CC)CC)C>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([N:19]3[CH2:23][CH2:22][CH2:21][C@H:20]3[CH2:24][N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[O:18])=[CH:14][CH:15]=2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 66723[1,1'-Biphenyl]-4-carboxylic acid, 4'-nitro-HCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidineHCID 2733179PyBroP

Product 1

HCID 57980075HCID 57980075, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Procedure NN: 4′-Nitro-biphenyl-4-carboxylic acid 200 mg (0.82 mmol), 152 mg of (S)(+)-1-(2-pyrrolidinylmethyl)pyrrolidine (0.99 mmol), 515 mg of bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP) (0.99 mmol) and 100 mg of triethylamine (0.99 mmol) are put into 5 ml of dichloromethane and stirred at room temperature for overnight. The reaction mixture is diluted with dichloromethane, washed by brine, dried over Na2SO4 and evaporated. The crude product is applied to silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=20:1), followed by SCX column to give the product. 163 mg (52%) Observed mass; 380 (M+1)

Workup

  1. washwashed by brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customto give the product

Sources & evidence

ORD record
ord-ea081e815c8d49499df128fe3745d430
Source dataset
uspto-grants-2011_08
Patent number
US08008301B2

Reaction notes

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