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HCID 66998054, compound → HCID 24936717, compound

HRID 561033
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Reaction equation

HRID 561033 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([F:41])=[CH:14][C:15]=1[C:16]1[C:21]2[S:22][C:23]([C:25]3[C:30]([F:31])=[CH:29][N:28]=[C:27]([NH:32][CH2:33][CH2:34][N:35]4[CH2:39][CH2:38][NH:37][C:36]4=[O:40])[N:26]=3)=[CH:24][C:20]=2[CH:19]=[CH:18][CH:17]=1)C)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[F:31][C:30]1[C:25]([C:23]2[S:22][C:21]3[C:16]([C:15]4[C:10]([CH2:9][NH:7][CH3:6])=[CH:11][N:12]=[C:13]([F:41])[CH:14]=4)=[CH:17][CH:18]=[CH:19][C:20]=3[CH:24]=2)=[N:26][C:27]([NH:32][CH2:33][CH2:34][N:35]2[CH2:39][CH2:38][NH:37][C:36]2=[O:40])=[N:28][CH:29]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 66998054HCID 66998054, compound

Product 1

HCID 24936717HCID 24936717, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent2×

Procedure

Dissolve [4-(2-{5-fluoro-2-[2-(2-oxo-imidazolidin-1-yl)-ethylamino]-pyrimidin-4-yl}-benzo[b]thiophen-7-yl)-6-fluoro-pyridin-3-ylmethyl]-methyl-carbamic acid tert-butyl ester (0.19 g, 0.32 mmol) in dry CH2Cl2 (1.4 mL) and CF3COOH (1.4 mL). Stir at room temperature for 1 hour. Remove solvent completely. Dilute the trifluoro-acetic acid salt with CH2Cl2. Wash with saturated NaHCO3 solution, water and saturated aqueous sodium chloride. Dry with MgSO4. After filtration, remove solvent. Dry in vacuo overnight to afford the title compound (0.12 g, 78%). MS (ES) m/z 495 [M+1]+.

Workup

  1. washWash with saturated NaHCO3 solution, water and saturated aqueous sodium chloride
  2. dry with materialDry with MgSO4
  3. filtrationAfter filtration
  4. customremove solvent
  5. customDry in vacuo overnight

Sources & evidence

ORD record
ord-f7ce5f861f3e4912a0c09d38b95f06d7
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063212B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes