HCID 66674649, compound → HCID 24938255, compound

HRID 422113Notes

Reaction equation

HRID 422113 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([F:38])=[CH:12][C:13]=1[C:14]1[C:19]2[S:20][C:21]([C:23]3[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH2:30][CH2:31][N:32]4[CH2:36][CH2:35][NH:34][C:33]4=[O:37])[N:24]=3)=[CH:22][C:18]=2[CH:17]=[CH:16][CH:15]=1)(C)(C)C>ClCCl>[NH3:7].[NH2:7][C:8]1[C:13]([C:14]2[C:19]3[S:20][C:21]([C:23]4[CH:28]=[CH:27][N:26]=[C:25]([NH:29][CH2:30][CH2:31][N:32]5[CH2:36][CH2:35][NH:34][C:33]5=[O:37])[N:24]=4)=[CH:22][C:18]=3[CH:17]=[CH:16][CH:15]=2)=[CH:12][C:11]([F:38])=[N:10][CH:9]=1

Participants

4

Reactant 1

HCID 66674649HCID 66674649, compound

Product 2

HCID 222AmmoniaYield 7%HCID 24938255HCID 24938255, compoundYield 8.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve the [6-fluoro-4-(2-{2-[2-(2-oxo-imidazolidin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophen-7-yl)-pyridin-3-yl]-carbamic acid tert-butyl ester into dichloromethane and adsorb onto silica gel (10 g) via concentration in vacuo. Dry under high vacuum for 24 hours. Place silica gel into a round bottom flask and heat in a temperature controlled oil bath to 98-99° C. while under high vacuum for 2 hours. Cool to room temperature. Extract product from silica gel with 10% 7 N ammonia in methanol/90% dichloromethane. Concentrate in vacuo. Chromatograph on silica eluting with a gradient of 100% dichloromethane to 7% 2 N ammonia in methanol/93% dichloromethane to afford the title compound (65.2 mg, 8.2%). MS (ES) m/z 450 [M+1]+.

Workup

  1. concentrationadsorb onto silica gel (10 g) via concentration in vacuo
  2. customDry under high vacuum for 24 hours
  3. temperaturePlace silica gel into a round bottom flask and heat in a temperature
  4. customto 98-99° C.
  5. customfor 2 hours
  6. concentrationConcentrate in vacuo

Sources & evidence

ORD record
ord-4dfc7ad1c9dc400e9cb57fea8051b1a2
Source dataset
uspto-grants-2012_01
Patent number
US08101628B2

Reaction notes

Loading…