Trifluoroacetic acid → HCID 58413201, compound

HRID 240651Notes

Reaction equation

HRID 240651 reaction equation
FC(F)(F)[C:3](O)=[O:4].C(OC([N:15]1[C@H:19]([CH2:20][OH:21])[CH2:18][C@H:17]([O:22][C:23]2[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=2[NH:30][C:31]2[C:32]3[C:39]([CH3:40])=[C:38]([C:41](N)=[O:42])[S:37][C:33]=3[N:34]=[CH:35][N:36]=2)[CH2:16]1)=O)(C)(C)C>ClCCl>[CH3:3][O:4][C:41]([C:38]1[S:37][C:33]2[N:34]=[CH:35][N:36]=[C:31]([NH:30][C:24]3[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=3[O:22][C@H:17]3[CH2:18][C@@H:19]([CH2:20][OH:21])[NH:15][CH2:16]3)[C:32]=2[C:39]=1[CH3:40])=[O:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58413158HCID 58413158, compound

Product 1

HCID 58413201HCID 58413201, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (1 ml) was added to a solution of 4-[2-((3S,5S)-1-tert-butoxycarbonyl-5-hydroxymethyl-pyrrolidin-3-yloxy)-4-fluoro-phenylamino]-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid amide (754 mg) in dichloromethane (10 ml). The reaction mixture was stirred for 4 h and a further aliqout of trifluoroacetic acid was added. The reaction mixture was stirred for 1 h again. The solvent was removed in vacuo. The mixture was diluted with dichloromethane and washed with 10% aq. K2CO3. The organic layer was concentrated and the residue was purified by flash column chromatography (silica gel, solvent: 100% dichloromethane→20:1:0,1 dichloromethane: MeOH: NH4OH)

Workup

  1. stirringThe reaction mixture was stirred for 1 h again
  2. customThe solvent was removed in vacuo
  3. additionThe mixture was diluted with dichloromethane
  4. washwashed with 10% aq. K2CO3
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by flash column chromatography (silica gel, solvent: 100% dichloromethane→20:1:0,1 dichloromethane: MeOH: NH4OH)

Sources & evidence

ORD record
ord-8f25f3ff9d244c5998a8bf4df6b47389
Source dataset
uspto-grants-2014_02
Patent number
US08648068B2

Reaction notes

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