1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274210, compound

HRID 1667097Notes

Reaction equation

HRID 1667097 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19](F)=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)O)=[CH:4][CH:3]=1.[O:23]=[C:24]1[C:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:27][CH2:26][N:25]1[CH2:41][C:42](O)=[O:43].Cl.C(N=C=NCCCN(C)C)C>ClCCl.CN(C)C1C=CN=CC=1>[C:5]1([C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[C:10]2[CH2:15][CH2:14][N:13]([C:42](=[O:43])[CH2:41][N:25]3[CH2:26][CH2:27][C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[C:24]3=[O:23])[CH2:12][CH2:11]2)[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 673590132-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetic acid

Product 1

HCID 45274210HCID 45274210, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of bis(4-fluorophenyl)(piperidin-4-yl)methanol (0.30 g, 1.00 mmol, Example 32A) 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 mixture 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 7.49-7.57 (m, 4H), 7.17-7.35 (m, 10H), 7.06-7.13 (m, 4H), 5.49 (s, 1H), 4.36 (d, J=14.0 Hz, 1H), 4.17 (d, J=16.6 Hz, 1H), 4.10 (d, J=15.7 Hz, 1H), 3.81 (d, J=14.3 Hz, 1H), 3.34 (t, J=6.7 Hz, 2H), 2.95-2.98 (m, 1H), 2.73-2.85 (m, 1H), 2.72 (t, J=6.6 Hz, 2H), 2.50-2.62 (m, 1H), 1.20-1.39 (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-557fda368b51454dab59195bd583cec6
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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