Cyclopropylamine → HCID 47451248, compound

HRID 515132Notes

Reaction equation

HRID 515132 reaction equation
[N:1]1[C:9]2[C:4](=NC=C[CH:8]=2)N(O)N=1.[C:11]([O:15][C:16]([NH:18][CH2:19][C:20]([OH:22])=O)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(N)CC1.Cl.C(N=C=NCCCN(C)C)C>CN(C1C=CN=CC=1)C.CN(C=O)C.C(OCC)(=O)C>[CH:9]1([NH:1][C:20](=[O:22])[CH2:19][NH:18][C:16](=[O:17])[O:15][C:11]([CH3:12])([CH3:13])[CH3:14])[CH2:4][CH2:8]1

Participants

8

Reactant 4

HCID 69828CyclopropylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 47451248HCID 47451248, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3H-[1,2,3]triazolo[4,5-b]pyridin-3-ol (7.77 g, 57.1 mmol), 2-(tert-butoxycarbonylamino)acetic acid (10 g, 57.1 mmol), cyclopropanamine (3.91 g, 68.5 mmol) and DMAP (8.37 g, 68.5 mmol) in DMF (28 mL) was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrogen chloride salt and the mixture stirred at room temperature for 16 h. The mixture was diluted with ethyl acetate, washed with 0.1N aqueous HCl, aqueous NaHCO3 and brine, dried over MgSO4, filtered and concentrated in vacuo to give tert-butyl 2-(cyclopropylamino)-2-oxoethylcarbamate (8.90 g, 41.5 mmol, 72.8%) as a pale yellow oil: 1H NMR (400 MHz, CDCl3) δ 6.18 (s, 1H), 3.74 (d, J=5.9 Hz, 2H), 2.71 (m, 1H), 1.45 (s, 9H); 0.84-0.7 (m, 2H), 0.56-0.43 (m, 2H); EIMS m/z 214 ([M]+). To a solution of tert-butyl 2-(cyclopropylamino)-2-oxoethylcarbamate (8.5 g, 39.7 mmol) in dioxane (20 mL) was added HCl (100 mmol, 25 mL 4 M in dioxane) and the mixture stirred at 10° C. for 3 h. The mixture was diluted with hexanes and filtered under vacuum to give 2-amino-N-cyclopropylacetamide, HCl salt as a white solid (5.2 g, 83%): mp 139-142° C.; 1H NMR (400 MHz, DMSO-d6) δ 8.66 (bs, 1H), 8.19 (bs, 3H), 3.46 (s, 2H), 2.73-2.60 (m, 1H), 0.71-0.60 (m, 2H), 0.48-0.36 (m, 2H).

Workup

  1. washwashed with 0.1N aqueous HCl, aqueous NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e038feb6c2c04b56a2dbb8938c500989
Source dataset
uspto-grants-2015_08
Patent number
US09108952B2

Reaction notes

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