Trifluoroacetic acid → 4-tert-Butyl-N-{5-fluoro-3-[6-(4-hydroxy-cyclohex-1-enyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methyl-phenyl}-benzamide

HRID 589502Notes

Reaction equation

HRID 589502 reaction equation
[C:1]([C:5]1[CH:40]=[CH:39][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([C:19]3[C:20]4[CH:27]=[C:26]([C:28]5[CH2:37][CH2:36][C:31]6(OCC[O:32]6)[CH2:30][CH:29]=5)[NH:25][C:21]=4[N:22]=[CH:23][N:24]=3)[C:13]=2[CH3:38])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:1]([C:5]1[CH:40]=[CH:39][C:8]([C:9]([NH:11][C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([C:19]3[C:20]4[CH:27]=[C:26]([C:28]5[CH2:37][CH2:36][CH:31]([OH:32])[CH2:30][CH:29]=5)[NH:25][C:21]=4[N:22]=[CH:23][N:24]=3)[C:13]=2[CH3:38])=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 712314624-tert-Butyl-N-{3-[6-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-5-fluoro-2-methyl-phenyl}-benzamide

Product 1

HCID 712308914-tert-Butyl-N-{5-fluoro-3-[6-(4-hydroxy-cyclohex-1-enyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-2-methyl-phenyl}-benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of Example 27 (450 mg, 0.832 mmol) and TFA (6 ml) in DCM (30 ml) was stirred at r.t. for 6 hrs. The solvents were removed in vacuo and the crude product was purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH gradient) to yield Intermediate 19.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by flash chromatography (silica gel, EtOAc/MeOH/NH4OH gradient)

Sources & evidence

ORD record
ord-6efca52f8599422bab2defa1e55891af
Source dataset
uspto-grants-2016_01
Patent number
US09233111B2

Reaction notes

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