1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 45274411, compound

HRID 1667273Notes

Reaction equation

HRID 1667273 reaction equation
[OH:1][NH:2]/[C:3](=[N:14]\[H])/[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[N:6][CH:5]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29](O)=O)[C:24]2=[O:32])=[CH:19][CH:18]=1.Cl.C(N=C=NCCCN(C)C)C>ClC(Cl)C>[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]2[CH2:27][CH2:26][N:25]([CH2:28][C:29]3[O:1][N:2]=[C:3]([C:4]4[CH:5]=[N:6][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:9]=4)[N:14]=3)[C:24]2=[O:32])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 673576422-(3-(4-Fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acidHCID 178506499HCID 178506499, compound

Product 1

HCID 45274411HCID 45274411, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

(Z)—N-Hydroxy-6-(trifluoromethyl)nicotinimidamide (0.082 g, 0.399 mmol), 2-(3-(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid (0.086 g, 0.363 mmol; Example 216A) and N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (0.104 g, 0.544 mmol) were stirred together in dichloroethane (1 mL) at room temperature for 4 hours. The reaction was heated to 85° C. and heated overnight. The reaction was cooled, loaded onto a GraceResolv™ 12 g silica gel column (Grace Davison Discovery Sciences) and the product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=36 mL/minute) over 30 minutes to give the title compound. 1H NMR (300 MHz, CDCl3) δ 9.41 (d, J=1.7, 1H), 8.58-8.50 (m, 1H), 7.84 (dd, J=0.5, 8.1, 1H), 7.33-7.26 (m, 2H), 7.11-7.01 (m, 2H), 4.98 (d, J=17.0, 1H), 4.87 (d, J=17.0, 1H), 3.78 (t, J=9.0, 1H), 3.74-3.61 (m, 2H), 2.67 (dddd, J=4.3, 7.0, 9.1, 13.2, 1H), 2.26 (ddd, J=8.5, 13.0, 16.5, 1H); MS (ESI+) m/z 407.0 (M+H)+.

Workup

  1. temperatureheated overnight
  2. temperatureThe reaction was cooled
  3. washthe product eluted with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes (Flow=36 mL/minute) over 30 minutes

Sources & evidence

ORD record
ord-d31c12a775854429bdbec6ce5d7a82f7
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

Loading…