Diisopropylethylamine → HCID 17757345, compound

HRID 1176063Notes

Reaction equation

HRID 1176063 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][C:5]([C:6]([N:8]2[CH2:12][CH2:11][CH:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[N:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[C:28](Cl)=[O:29].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:15][N:13]([CH3:14])[CH:10]1[CH2:11][CH2:12][N:8]([C:6]([C:5]2[CH:16]=[CH:17][C:2]([NH:1][C:28]([C:19]3[CH:20]=[CH:21][C:22]4[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=3)=[O:29])=[CH:3][CH:4]=2)=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2760547Quinaldoyl chlorideHCID 225674711-(4-Aminobenzoyl)-3-dimethylamino-pyrrolidine

Product 1

HCID 17757345HCID 17757345, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(4-aminobenzoyl)-3-dimethylamino-pyrrolidine (46 mg, 0.2 mmol), quinoline-2-carbonyl chloride (38 mg, 0.2 mg) and diisopropyl ethyl amine (0.1 mL, 0.6 mmol) in CH2Cl2 is stirred at room temperature for 5 h and concentrated in vacuo. The resultant residue is dissolved in a mixture of DMSO, methanol and water and purified by reverse-phase semi-preparative HPLC, using the same HPLC conditions described in Example 1, to give the title compound as a white powder (10mg), identified by HPLC and mass spectral analyses. Retention Time, MS [366.2 m/e (M+H)].

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resultant residue is dissolved in a mixture of DMSO, methanol and water
  3. custompurified by reverse-phase semi-preparative HPLC

Sources & evidence

ORD record
ord-54881e31066c42efa98edfe90c906860
Source dataset
uspto-grants-2010_11
Patent number
US07842715B2

Reaction notes

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