Diisopropylethylamine → HCID 71466597, compound

HRID 1746363Notes

Reaction equation

HRID 1746363 reaction equation
[CH3:1][NH:2][CH2:3][C:4]([NH:6][CH2:7][CH2:8][NH:9][C:10](=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31])=[O:5].C(OC([NH:40][C:41](=NC(=O)OC(C)(C)C)[N:42]1C=CC=N1)=O)(C)(C)C.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][N:2]([CH2:3][C:4]([NH:6][CH2:7][CH2:8][NH:9][C:10](=[O:32])[CH2:11][CH2:12]/[CH:13]=[CH:14]\[CH2:15]/[CH:16]=[CH:17]\[CH2:18]/[CH:19]=[CH:20]\[CH2:21]/[CH:22]=[CH:23]\[CH2:24]/[CH:25]=[CH:26]\[CH2:27]/[CH:28]=[CH:29]\[CH2:30][CH3:31])=[O:5])[C:41]([NH2:42])=[NH:40]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 4428040N,N'-Bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidineHCID 86673201HCID 86673201, compound

Product 1

HCID 71466597HCID 71466597, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2-(Methylamino)acetamido)ethyl)docosa-4,7,10,13,16,19-hexaenamide (416 mg, 1.2 mmol) was taken up in 10 mL of DMF along with tert-butyl (((tert-butoxycarbonyl)amino)(1H-pyrazol-1-yl)methylene)carbamate (154 mg, 1.2 mmol) and DIEA (154 mg, 1.2 mmol). The resulting reaction mixture was stirred at room temperature for 24 h. It was then diluted with EtOAc and washed with water. The organic layer was washed with brine, dried (Na2SO4) and concentrated under reduced pressure. Purification by silica gel chromatography (pentane/EtOAc) afforded 350 mg of the di-Boc derivative of (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-(2-(1-methylguanidino)acetamido)ethyl)docosa-4,7,10,13,16,19-hexaenamide (43% yield). MS (EI) calcd for C32H51N3O4 541.39. found 542 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customPurification by silica gel chromatography (pentane/EtOAc)

Sources & evidence

ORD record
ord-3aa4ddfa3ef44aed95cfcec097cc420b
Source dataset
uspto-grants-2015_10
Patent number
US09150504B2

Reaction notes

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