1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67539214, compound

HRID 1192446Notes

Reaction equation

HRID 1192446 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[C:22]([CH2:29][CH2:30][CH2:31][C:32]([NH2:44])([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:33]([OH:35])=O)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].Cl.Cl.[N:47]1([C:53]2[C:62]3[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=3)[N:56]=[CH:55][N:54]=2)[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1>CN(C=O)C.O>[C:22]([CH2:29][CH2:30][CH2:31][C:32]([NH2:44])([CH2:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1)[C:33]([N:50]1[CH2:51][CH2:52][N:47]([C:53]2[C:62]3[C:57](=[CH:58][CH:59]=[CH:60][CH:61]=3)[N:56]=[CH:55][N:54]=2)[CH2:48][CH2:49]1)=[O:35])([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23]

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 66570482HCID 66570482, compoundHCID 67538241HCID 67538241, compound

Product 1

HCID 67539214HCID 67539214, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of EDCI (100 mg, 0.54 mmol), HOBt.H20 (82 mg, 0.54 mmol), 5-Boc-amino-2-(4-chlorobenzyl)-pentanoic acid (170 mg, 0.50 mmol), and TEA (190 μL, 1.4 mmol) in 3 mL DMF was stirred 10 minutes, and solid 4-piperazin-1-yl-quinazoline dihydrochloride (130 mg, 0.45 mmol) was added. The reaction mixture was stirred at room temperature 15 hours, after which water was added. The reaction mixture was extracted with DCM, and combined extracts washed with sat NaHCO3, dried (Na2SO4), filtered, and concentrated. The crude was purified on silica gel (1:1 to 1:9 DCM:EtOAc) to give 5-Boc-amino-2-(4-chlorobenzyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-pentan-1-one. LCMS (APCI+) m/z 538 [M+H]+; Rt: 3.12 min.

Workup

  1. extractionThe reaction mixture was extracted with DCM
  2. washwashed with sat NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified on silica gel (1:1 to 1:9 DCM:EtOAc)

Sources & evidence

ORD record
ord-95f68ed3b8d24933b35727d80a08bf70
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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