Trifluoroacetic acid → HCID 22249208, compound

HRID 2247291Notes

Reaction equation

HRID 2247291 reaction equation
C([N:14]1[CH2:17][CH:16]([O:18][C:19]2[CH:24]=[C:23]([CH2:25][NH:26][C:27]3[N:45]=[CH:44][CH:43]=[CH:42][C:28]=3[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=3)=[O:30])[CH:22]=[CH:21][N:20]=2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1.[SiH](CC)(CC)CC.C(O)(C(F)(F)F)=O>>[NH:14]1[CH2:15][CH:16]([O:18][C:19]2[CH:24]=[C:23]([CH2:25][NH:26][C:27]3[N:45]=[CH:44][CH:43]=[CH:42][C:28]=3[C:29]([NH:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=3)=[O:30])[CH:22]=[CH:21][N:20]=2)[CH2:17]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 22249332HCID 22249332, compound

Product 1

HCID 22249208HCID 22249208, compound

Procedure

2-{[2-(1-Benzhydryl-azetidin-3-yloxy)-pyridin-4-ylmethyl]-amino}-N-(4-tert-butyl-phenyl)-nicotinamide (210 mg) was heated at reflux with Et3SiH (5 ml) and TFA (15 ml) for 9 h. The mixture was concentrated, then diluted with CH2Cl2 (50 ml) and washed with sat'd NaHCO3 (50 ml) and brine (30 ml), dried over MgSO4 and purified by silica gel chromatography (10% MeOH/2M NH3 90% EtOAc) to afford the product as a yellow solid. M+H 432.5. Calc'd for C25H29N5O2: 431.2.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with CH2Cl2 (50 ml)
  3. washwashed with sat'd NaHCO3 (50 ml) and brine (30 ml)
  4. dry with materialdried over MgSO4
  5. custompurified by silica gel chromatography (10% MeOH/2M NH3 90% EtOAc)

Sources & evidence

ORD record
ord-1b574c286331442da1b74fbfeaf3bc52
Source dataset
uspto-grants-2010_03
Patent number
US07687643B2

Reaction notes

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