Diisopropylethylamine → HCID 178521305, compound

HRID 380176Notes

Reaction equation

HRID 380176 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][C@H:12]([C:19]([N:21]([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=2)[CH2:22][C:23](O)=[O:24])=[O:20])[CH2:13][C:14]2[N:18]=[CH:17][NH:16][CH:15]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.[N:84]1[CH:89]=[CH:88][CH:87]=[CH:86][C:85]=1[CH2:90][CH2:91][NH2:92]>C(Cl)Cl>[CH2:7]([O:8][C:9](=[O:10])[NH:11][CH:12]([C:19](=[O:20])[N:21]([CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[CH:31][CH:32]=1)[CH2:22][C:23](=[O:24])[NH:92][CH2:91][CH2:90][C:85]1[CH:86]=[CH:87][CH:88]=[CH:89][N:84]=1)[CH2:13][C:14]1[N:18]=[CH:17][NH:16][CH:15]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 212496Pyridine, 2-(2-aminoethyl)-, hydrochlorideHCID 2724699PyBOPHCID 178525870HCID 178525870, compound

Product 1

HCID 178521305HCID 178521305, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the acid from Step 3 (0.33 g, 0.61 mmol) in methylene chloride was added PyBOP (0.67 g, 1.3 mmol) and diisopropylethylamine (0.23 mL, 1.3 mmol) followed by 2-pyridineethaneamine hydrochloride (0.082 g, 0.67 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, the residue taken up in ethyl acetate, which was washed 3 times with saturated NaHCO3, brine, dried over MgSO4, and concentrated. Flash chromatography gave 0.156 g (37%) of the title compound as a white foam; ES-MS 647 (m+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwhich was washed 3 times with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0851ab74b83148cbab9df051b99eba73
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

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