Ethyl Acetate → HCID 57955170, compound

HRID 73696Notes

Reaction equation

HRID 73696 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[NH2:23][C:24]1[C:29]2=[C:30]([C:43]3[CH:48]=[CH:47][C:46]([NH:49][C:50]([NH:52][C:53]4[CH:58]=[C:57]([C:59]([F:62])([F:61])[F:60])[CH:56]=[CH:55][N:54]=4)=[O:51])=[CH:45][CH:44]=3)[C:31]([CH:40]([OH:42])[CH3:41])=[C:32]([CH2:33][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)[N:28]2[N:27]=[CH:26][N:25]=1.C([O-])(O)=O.[Na+].CCOC(C)=O>CS(C)=O.O>[C:40]([C:31]1[C:30]([C:43]2[CH:48]=[CH:47][C:46]([NH:49][C:50]([NH:52][C:53]3[CH:58]=[C:57]([C:59]([F:60])([F:61])[F:62])[CH:56]=[CH:55][N:54]=3)=[O:51])=[CH:45][CH:44]=2)=[C:29]2[N:28]([C:32]=1[CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)[N:27]=[CH:26][N:25]=[C:24]2[NH2:23])(=[O:42])[CH3:41]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57955308N-{4-[4-amino-6-(1-hydroxyethyl)-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]-triazin-5-yl]phenyl}-N'-[4-(trifluoromethyl)-pyridin-2-yl]urea

Product 1

HCID 57955170HCID 57955170, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

Dess-Martin periodinane (342.9 mg, 0.809 mmol) was added to a stirring solution of N-{4-[4-amino-6-(1-hydroxyethyl)-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]-triazin-5-yl]phenyl}-N′-[4-(trifluoromethyl)-pyridin-2-yl]urea (300 mg, 0.54 mmol) in DMSO (3 mL). The reaction was allowed to stir until complete by HPLC. Saturated aq. NaHCO3 solution (0.25 volumes) was added until a lot of solid had crashed out. Then 2 volumes of EtOAc and 0.5 volumes of H2O was added. This was allowed to stir overnight and the next day the excess liquid was removed via pipette. Careful addition of 5-10 mL of Et2O and 2 mL of CH2Cl2 provided an off white suspension. This was filtered to give a the title compound (100 mg, 0.18 mmol, 31% yield, 2 steps) as pure white powder. 1H-NMR (DMSO-d6). δ 10.20 (s, 1H), 10.04 (s, 1H), 8.67 (d, J=5.1 Hz, 1H), 8.20 (s, 1H), 8.10 (s, 1H), 7.78 (d, J=8.7 Hz, 2H), 7.52-7.48 (m, 3H), 4.19 (s, 2H), 3.63-3.60 (m, 4H), 2.56-2.53 (m, 4H), 2.19 (s, 3H). MS [M+H]+=555; LCMS RT=2.51 min.

Workup

  1. stirringto stir overnight
  2. customthe next day the excess liquid was removed via pipette
  3. additionCareful addition of 5-10 mL of Et2O and 2 mL of CH2Cl2
  4. customprovided an off white suspension
  5. filtrationThis was filtered

Sources & evidence

ORD record
ord-96cc1d01de66483981e91e5751efafcc
Source dataset
uspto-grants-2014_09
Patent number
US08829185B2

Reaction notes

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