1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 87735512, compound

HRID 2214280Notes

Reaction equation

HRID 2214280 reaction equation
CCN=C=NCCCN(C)C.Cl.[C:13]([O:17][C:18](=[O:50])[CH2:19][CH:20]([C:33](=[O:49])[N:34]([C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:39][CH:38]=1)[CH2:35][CH3:36])[CH:21]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:22](O)=[O:23])([CH3:16])([CH3:15])[CH3:14].[C:51]([O:70][NH2:71])([C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>O.C1COCC1>[C:13]([O:17][C:18](=[O:50])[CH2:19][CH:20]([C:33](=[O:49])[N:34]([C:37]1[CH:38]=[CH:39][C:40]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:41][CH:42]=1)[CH2:35][CH3:36])[CH:21]([C:22](=[O:23])[NH:71][O:70][C:51]([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)([C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3015602O-(triphenylmethyl)hydroxylamineHCID 69212306HCID 69212306, compound

Product 1

HCID 87735512HCID 87735512, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

WSC.HCl (683 mg, 3.49 mmol) was dissolved in water (1 mL) and the pH was adjusted to 4.8. The compound of Example 55 (300 mg, 0.582 mmol) was dissolved in the same amount of THF and added to the former solution. O-Trityl hydroxylamine (505 mg, 1.746 mmol) was added and the mixture was stirred for 24 h. The reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate. The water phase was extracted several times with ethyl acetate. The recombined organic layer was washed with brine, a saturated sodium hydrogen carbonate solution, and brine. The solvent was evaporated, following drying over sodium sulfate, and the crude was flashed with 30% ethyl acetate in hexanes. 1H NMR(CDCl3, 400 MH: 1.32(s, 9H); 1.50(m, 1H); 1.74(m, 1H); 2.32(m, 6H); 2.53(m, 2H); 3.46(m, 2H); 7.00(m, 1H); 7.16–7.57(m, 30H); FAB: 774(MH+).

Workup

  1. additionadded to the former solution
  2. customThe reaction mixture was partitioned between HCl (0.5N, excess) and ethyl acetate
  3. extractionThe water phase was extracted several times with ethyl acetate
  4. washThe recombined organic layer was washed with brine
  5. customThe solvent was evaporated
  6. dry with materialfollowing drying over sodium sulfate

Sources & evidence

ORD record
ord-13cd911cba73489da88e916b92ee39a3
Source dataset
uspto-grants-2006_09
Patent number
US07105539B2

Reaction notes

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