1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274307, compound

HRID 1667098Notes

Reaction equation

HRID 1667098 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[OH:8])[CH2:3][CH2:2]1.[O:29]=[C:30]1[C:34]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH2:33][CH2:32][N:31]1[CH2:47][C:48](O)=[O:49].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[OH:8][C:7]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:26])([F:27])[F:28])[CH:20]=1)([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:17])[F:18])[CH:10]=1)[CH:4]1[CH2:5][CH2:6][N:1]([C:48](=[O:49])[CH2:47][N:31]2[CH2:32][CH2:33][C:34]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:30]2=[O:29])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acidHCID 86640834HCID 86640834, compound

Product 1

HCID 45274307HCID 45274307, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of piperidin-4-ylbis(3-(trifluoromethyl)phenyl)methanol (0.40 mg, 1.00 mmol, Example 33A) in dichloromethane (20 mL) was added 2-(2-oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid (Example 1C, 0.30 g, 1.00 mmol) under nitrogen. To the reaction was added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.38 g, 2.00 mmol) and N,N-dimethylpyridin-4-amine (6.1 mg, 0.005 mmol), and the reaction mixture was stirred overnight at room temperature. The reaction was concentrated, and the residue was partitioned in ethyl acetate:water (8:2). The organic layer was separated, washed with water and then brine, dried over MgSO4, filtered and concentrated. Silica gel chromatography eluting with ethyl acetate/hexanes (1:1) gave the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.85-7.93 (m, 4H), 7.55-7.57 (m, 4H), 7.18-7.36 (m, 10H), 5.93 (s, 1H), 4.34-4.41 (m, 1H), 4.06-4.23 (m, 2H), 3.82 (d, J=13.5 Hz, 1H), 3.35 (t, J=6.9 Hz, 2H), 2.94-3.11 (m, 2H), 2.72 (t, J=6.4 Hz, 2H), 2.59-2.67 (m, 1H), 1.17-1.50 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residue was partitioned in ethyl acetate:water (8:2)
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washSilica gel chromatography eluting with ethyl acetate/hexanes (1:1)

Sources & evidence

ORD record
ord-2fb18a3be16a48709d3804399e560ae2
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…