1,1'-Carbonyldiimidazole → HCID 25116909, compound

HRID 2093032Notes

Reaction equation

HRID 2093032 reaction equation
N=C=N.C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)C(O)=O.[CH3:23][N:24]([S:53]([CH3:56])(=[O:55])=[O:54])[C:25]1[C:30]([CH2:31][NH:32][C:33]2[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][N:36]=[C:35]([NH:43][C:44]3[CH:45]=[C:46]([CH:50]=[CH:51][CH:52]=3)[C:47]([OH:49])=O)[N:34]=2)=[CH:29][CH:28]=[CH:27][N:26]=1.CC[N:59]([CH:63]([CH3:65])[CH3:64])C(C)C.C1(N)CC1>C(#N)C>[CH:63]1([NH:59][C:47](=[O:49])[C:46]2[CH:50]=[CH:51][CH:52]=[C:44]([NH:43][C:35]3[N:34]=[C:33]([NH:32][CH2:31][C:30]4[C:25]([N:24]([CH3:23])[S:53]([CH3:56])(=[O:54])=[O:55])=[N:26][CH:27]=[CH:28][CH:29]=4)[C:38]([C:39]([F:42])([F:40])[F:41])=[CH:37][N:36]=3)[CH:45]=2)[CH2:65][CH2:64]1

Participants

7

Reactant 5

HCID 682631,1'-CarbonyldiimidazoleHCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 160435CarbodiimideHCID 86627982HCID 86627982, compound

Product 1

HCID 25116909HCID 25116909, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A polymer supported carbodiimide (PS-CDI) (0.326 mmol) was allowed to swell in acetonitrile (volume of 500 μL). The resultant suspension was treated with 10 (100 mg, 0.164 mmol) and DIEA (29 μL, 0.164 mmol). The resultant solution was then treated with cyclopropylamine (19 μL, 0.164 mmol). The resultant suspension was then mixed on a shaker plate for 16 hours. The mixture was then filtered, and the solids washed with 10% MeOH in chloroform. The combined filtrates were concentrated under reduced pressure, and the resultant residue was purified over silica (99:1:0.1 CHCl3:CH3OH:NH4OH) to provide 11 as a white foam. Yield: 14.3 mg, 16%. LC Ret. Time (standard)=2.1 min., m/z 536.2 (MH+); 1H NMR (CD3OD) δ: 8.42 (d, J=7.8 Hz., 1 H), 8.20 (s, 1 h), 7.97 (t, J=7.8 Hz., 1H), 7.81 (d, J=7.8 Hz., 1H), 1.68 (d, J=7.8 Hz., 1H), 7.39-7.34 (m, 2H), 7.26 (t, J=7.8 Hz., 1H), 4.94 (s, 2H), 3.23 (s, 3H), 3.14 (s, 3H), 2.82 (m, 1H), 0.79 (m, 2 h), 0.60 (m, 2H) ppm. FAK IC50: 0.00186 μM

Workup

  1. filtrationThe mixture was then filtered
  2. washthe solids washed with 10% MeOH in chloroform
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customthe resultant residue was purified over silica (99:1:0.1 CHCl3:CH3OH:NH4OH)

Sources & evidence

ORD record
ord-ac520b2ac4324b2ca894edd625b787c3
Source dataset
uspto-grants-2013_05
Patent number
US08440822B2

Reaction notes

Loading…