1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 23511784, compound

HRID 350406Notes

Reaction equation

HRID 350406 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[CH2:6][NH:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][CH:13]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:38][C:39](O)=[O:40])[CH:24]=[CH:25][C:26]=1[NH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:29].CCN=C=NCCCN(C)C.Cl>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH2:38][C:39]([N:1]2[CH2:5][CH2:4][CH2:3][CH:2]2[CH2:6][NH:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:12][CH:13]=2)=[O:40])[CH:24]=[CH:25][C:26]=1[NH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[CH3:37])=[O:29]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acidHCID 23512101HCID 23512101, compound

Product 1

HCID 23511784HCID 23511784, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of ethyl 5-[(2-pyrrolidinyl)methylamino]pyridine-2 carboxylate (230 mg, 0.923 mmol), 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (290 mg, 0.923 mmol), 4-DMAP (145 mg, 1.15 mmol) in DMF (7 ml) was added EDC.HCl (225 mg, 1.15 mmol) at room temperature. The resulting mixture was stirred at room temperature for 20 hr. The mixture was pored into ice-water. The solid was collected, washed with water and air-dried. The crude solid was purified by silica gel (30 ml) column chromatography with CHCl3-EtOH (98:2, v/v) as eluent to give ethyl 5-[[1-[3-methoxy4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]pyridine-2-carboxylate (400 mg, 80%) as fine needles. IR (KBr) n 3325, 1709, 1618, 1585, 1531 cm−; 1H-NMR (CDCl3) δ 1.39 (t, J=7 Hz, 3 H), 1.73–2.07 (series of m, 4 H), 2.28 (s, 3 H), 3.12 and 3.49 (each m, each 1 H), 3.60 (s, 2 H), 4.39 (br q, J=7 Hz, 2 H), 4.53 (m, 1 H), 6.07 (br s, 1 H), 6.23 (br s, 1 H), 6.75–6.77 (series of s and m, 2 H), 6.82 (dd, J=3.0 and 8.5 Hz, 1 H), 7.09–7.22 (series of m, 3 H), 7.49 (d, J=8.0 Hz, 1 H), 7.90 (d, J=8.5 Hz, 1H), 7.98 (d, J=2.6 Hz, 1H), 8.06 (d, J=8.8 Hz, 1H); MS (FAB) m/z 546 (M++1); Anal. Calcd for C30H35N5O5.1.5×H2O: C, 52.92; H, 6.69; N, 12.23. Found: C, 63.11; H, 6.48; N, 11.96.

Workup

  1. customThe solid was collected
  2. washwashed with water
  3. customair-dried
  4. customThe crude solid was purified by silica gel (30 ml) column chromatography with CHCl3-EtOH (98:2

Sources & evidence

ORD record
ord-86fa245e671c47dfa2404ec56cd61447
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

Loading…