HCID 10894751, compound → HCID 11731371, compound

HRID 1793121Notes

Reaction equation

HRID 1793121 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11](I)[NH:12][C:13]=1[CH2:14][CH2:15][CH3:16])=[O:8]>CO>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[C:19]([F:21])[CH:20]=1)[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:11]2[NH:12][C:13]([CH2:14][CH2:15][CH3:16])=[C:9]([C:7]([NH:6][CH2:5][C:4]3[CH:18]=[C:19]([F:21])[CH:20]=[C:2]([F:1])[CH:3]=3)=[O:8])[N:10]=2)[NH:12][C:13]=1[CH2:14][CH2:15][CH3:16])=[O:8]

Participants

3

Reactant 1

HCID 10894751HCID 10894751, compound

Product 1

HCID 11731371HCID 11731371, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Iodide 6b (0.44 g; 1.1 mmol) was used as starting material. After cooling to rt, the reaction mixture was diluted with CH3OH and filtered. The filtrate was evaporated under vacuum, and the residue was dissolved in CHCl3. Slow addition of CH3CN caused a brown solid to precipitate. This material was collected by filtration and washed with CH3CN to afford 0.12 g (40%) of 1b as an off-white solid. mp 173–174 C; TLC (CH2Cl2-EtOAc, 1:1): Rf=0.51; 1H NMR (DMSO-d6): δ 0.85 (t, 6H), 1.60 (m, 4H), 2.90 (t, 4H), 4.42 (d, 4H), 6.99 (d, 411), 7.05 (t, 2H), 8.20 (br t, 2H); 13C NMR (DMSO-d6): δ 14.1, 23.1, 30.2, 41.8, 110.9, 131.0, 141.7, 145.5, 161.3, 163.8, 164.7; UV/vis (CH3OH): max (M−1cm−1)=287 (21800), 294 (20700), 309 (10700); LRMS (CI+): m/z (%): 557 (100) [M+H]+; HRMS (CI+): calcd for C28H29F4 N6O2 557.2288; found 557.2292.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated under vacuum
  3. dissolutionthe residue was dissolved in CHCl3
  4. additionaddition of CH3CN
  5. customto precipitate
  6. filtrationThis material was collected by filtration
  7. washwashed with CH3CN

Sources & evidence

ORD record
ord-0530478446b848d8948fd58216e836f3
Source dataset
uspto-grants-2006_07
Patent number
US07078528B2

Reaction notes

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