1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → [7-(3-Tert-butoxycarbonylamino-propylcarbamoyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester

HRID 2302007Notes

Reaction equation

HRID 2302007 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([C:16]([OH:18])=O)=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:19])=[O:4].O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[C:43]([O:47][C:48](=[O:54])[NH:49][CH2:50][CH2:51][CH2:52][NH2:53])([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][O:2][C:3](=[O:4])[CH2:5][CH:6]1[CH2:15][C:14]2[C:9](=[CH:10][C:11]([C:16](=[O:18])[NH:53][CH2:52][CH2:51][CH2:50][NH:49][C:48]([O:47][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:54])=[CH:12][CH:13]=2)[NH:8][C:7]1=[O:19]

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 27960291-Hydroxybenzotriazole hydrateHCID 184626573-Methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-carboxylic Acid

Product 1

HCID 69980580[7-(3-Tert-butoxycarbonylamino-propylcarbamoyl)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid methyl ester

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methoxycarbonylmethyl-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carboxylic acid (1.0 g, 3.8 mmol) in DMF (20 mL) at 25° C. was added 1-hydroxy-benzotriazole hydrate (HOBT) (0.565 g, 4.18 mmol). The solution was cooled to 0° C. and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (DAEC) (0.801 g, 4.18 mmol) was added. After 10 min the reaction mixture was allowed to warm to 25° C. After 2 h triethylamine (1.3 mL) was added and tert-butyl-N(3-aminopropyl)carbamate (0.66 g, 3.8 mmol) added after 30 minutes. After 20 h ethyl acetate was added and the mixture washed with 0.1 N aqueous hydrochloric acid (3×), aqueous sodium bicarbonate (3×) and brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo to give the title compound as a light brown powder. NMR (dmso-d6, 200 MHz) : δ1.4 (s, 9H, tert-butyl), 1.6 (m, 2H, CH2), 2.7-3.3 (m, 9H, CH2CHCH2, NCH2, NCH2), 3.6 (s, 3H, CH3), 6.8 (t, 1H, NH), 7.2-7.4 (m, 3H, ArH), 8.3 (t, 1H, NH), 10.3 (s, 1 H. NH).

Workup

  1. temperatureto warm to 25° C
  2. washthe mixture washed with 0.1 N aqueous hydrochloric acid (3×), aqueous sodium bicarbonate (3×) and brine
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e94b14c47e2349969c63b955e64b2368
Source dataset
uspto-grants-2002_08
Patent number
US06429214B1

Reaction notes

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