Triethylamine → HCID 67130781, compound

HRID 1746600Notes

Reaction equation

HRID 1746600 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[CH:19]=[CH:18][CH:17]=[CH:16][C:10]=1[CH:11]=[CH:12][C:13]([OH:15])=O.CCN=C=NCCCN(C)C.Cl.Cl.[CH2:33]([N:35]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:37]([CH2:38][C@@H:39]([C:41]([O:43][CH3:44])=[O:42])[NH2:40])=[CH:36]1)[CH3:34]>C(Cl)Cl>[CH2:33]([N:35]1[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[C:37]([CH2:38][C@@H:39]([C:41]([O:43][CH3:44])=[O:42])[NH:40][C:13](=[O:15])[CH:12]=[CH:11][C:10]2[CH:16]=[CH:17][CH:18]=[CH:19][C:9]=2[F:8])=[CH:36]1)[CH3:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 679773-(2-Fluorophenyl)prop-2-enoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67312025HCID 67312025, compound

Product 1

HCID 67130781HCID 67130781, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.5 mL), 2-fluorocinnamic acid (1.8 g) and WSC.HCl (2.1 g) were at 0° C. added to methylene chloride (70 mL) suspension of the compound obtained in Example 143 (2.8 g). The mixture was stirred for 4 hours at room temperature. The reaction mixture was washed with water, and thereafter the organic layer was dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under a reduced pressure was purified with silica gel column chromatography (chloroform), to give the captioned compound (2.7 g, 70%) as crystals.

Workup

  1. customwere at 0° C.
  2. washThe reaction mixture was washed with water
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under a reduced pressure
  6. customwas purified with silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-0ca2c565cd474f928880272048898dfc
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

Loading…