1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 69334706, compound

HRID 354418Notes

Reaction equation

HRID 354418 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].[CH3:24][O:25][C:26]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][C@@H:36]2[CH2:40][C@H:39]([O:41][C:42]3[CH:51]=[CH:50][C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH:43]=3)[CH2:38][NH:37]2)=[N:32][CH:33]=1)=[O:27].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:24][O:25][C:26]([C:28]1[CH:29]=[CH:30][C:31]([O:34][CH2:35][C@@H:36]2[CH2:40][C@H:39]([O:41][C:42]3[CH:51]=[CH:50][C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH:43]=3)[CH2:38][N:37]2[C:21](=[O:23])[CH2:20][C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=2)=[N:32][CH:33]=1)=[O:27]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 69332896HCID 69332896, compound

Product 1

HCID 69334706HCID 69334706, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (89 mg, 0.283 mmol), methyl-2-[(2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate (107 mg, 0.78 mmol), EDC.HCl (81 mg, 0.425 mmol) and DMAP (52 mg, 0.425 mmol) in DMF (3 ml) was stirred at room temperature for 18 h. The mixture was poured into ice water and extracted with EtOAc. The combined extracts were washed with ice water and brine. After dried over Na2SO4, the extracts were concentrated in vacuo. The residue was purified on TLC [CHCl3/MeOH (10/1)], to give 2-[(2S,4S)-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxy-5-pyridinecarboxylic acid methyl ester (193 mg, 100%) as a colorless amorphous. 1H-NMR (CDCl3) δ2.27 (d, J=3.2 Hz, 3H), 2.30 (m, 1H), 2.49 (dd, J=14.2, 2.0 Hz, 1H), 3.60 (d, J=3.9 Hz, 1H), 3.67 (d, J=5.9 Hz, 3H), 3.81 (s, 1H), 3.85 (s, 1H), 3.88 and 3.91 (s, 3H, amide isomers), 3.95 (m, 1H), 4.02-5.09 (m, 4H), 6.67 (d, J=8.8 Hz, 1H), 6.73-7.13 (m, 3H), 7.20-7.45 (m, 7H), 7.53 (t, J=7.8 Hz, 1H), 7.67-7.77 (m, 3H), 8.02-8.84 (m, 3H).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with ice water and brine
  3. dry with materialAfter dried over Na2SO4
  4. concentrationthe extracts were concentrated in vacuo
  5. customThe residue was purified on TLC [CHCl3/MeOH (10/1)]

Sources & evidence

ORD record
ord-e935a9f6f4fa48f0803efb5e6a6d9c8b
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

Loading…