1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67129301, compound

HRID 1661116Notes

Reaction equation

HRID 1661116 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([NH:14][NH2:15])=[N:12][N:11]([CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=3)[C:10](=[O:28])[C:9]=2[C:29]2[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][CH:30]=2)=[CH:4][CH:3]=1.[C:37]([NH:44][C@H:45]([C:47](O)=[O:48])C)([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([NH:14][NH:15][C:47](=[O:48])[CH2:45][NH:44][C:37](=[O:38])[O:39][C:40]([CH3:41])([CH3:42])[CH3:43])=[N:12][N:11]([CH2:16][C:17]3[C:18]([CH3:27])=[N:19][C:20]([C:23]([F:25])([F:26])[F:24])=[CH:21][CH:22]=3)[C:10](=[O:28])[C:9]=2[C:29]2[CH:30]=[CH:31][C:32]([C:33]#[N:34])=[CH:35][CH:36]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 85082Tert-butoxycarbonylalanineHCID 671287294-(5-(4-Chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile

Product 1

HCID 67129301HCID 67129301, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 4-(5-(4-chlorophenyl)-6-hydrazinyl-2-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydropyridazin-4-yl)benzonitrile (70 mg, 0.1367 mmol), N-Boc-alanine (24 mg, 0.1367 mmol), EDAC (30 mg, 0.150 mmol), HOBT (20.3 mg, 0.150 mmol) THF (5 ml) and diisopropyl ethyl amine (0.026 ml, 0.150 mmol). The reaction was stirred at rt for 5 hr. After this time the reaction mixture was diluted with EtOAc (25 ml). The resulting solution was washed with water (2×15 ml) and saturated NaCl (15 ml). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by silica gel column chromatography (8 g silica gel) eluting with a gradient of 20%-100% EtOAc/Hex to give product tert-butyl 2-(2-(4-(4-chlorophenyl)-5-(4-cyanophenyl)-1-((2-methyl-6-(trifluoromethyl)pyridin-3-yl)methyl)-6-oxo-1,6-dihydropyridazin-3-yl)hydrazinyl)-2-oxoethylcarbamate as a light yellow solid (54 mg, 60% yield)

Workup

  1. washThe resulting solution was washed with water (2×15 ml) and saturated NaCl (15 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel column chromatography (8 g silica gel)
  6. washeluting with a gradient of 20%-100% EtOAc/Hex

Sources & evidence

ORD record
ord-9c37e7dc51af4decb737cd747ccca560
Source dataset
uspto-grants-2011_10
Patent number
US08030306B2

Reaction notes

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