Trifluoroacetic acid → 4-amino-N-(1-(4-chlorophenyl)-2-hydroxyethyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide

HRID 422983Notes

Reaction equation

HRID 422983 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([NH:11][C:12]([C:14]2([NH:29]C(=O)OC(C)(C)C)[CH2:19][CH2:18][N:17]([C:20]3[C:21]4[CH:28]=[CH:27][NH:26][C:22]=4[N:23]=[CH:24][N:25]=3)[CH2:16][CH2:15]2)=[O:13])[CH2:9][OH:10])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>>[NH2:29][C:14]1([C:12]([NH:11][CH:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:9][OH:10])=[O:13])[CH2:15][CH2:16][N:17]([C:20]2[C:21]3[CH:28]=[CH:27][NH:26][C:22]=3[N:23]=[CH:24][N:25]=2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57750378tert-Butyl 4-(1-(4-chlorophenyl)-2-hydroxyethylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate2×

Product 1

HCID 426021764-amino-N-(1-(4-chlorophenyl)-2-hydroxyethyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamideYield 99.1%

Procedure

tert-Butyl 4-(1-(4-chlorophenyl)-2-hydroxyethylcarbamoyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-4-ylcarbamate (Intermediate 18) (137 mg, 0.27 mmol) was treated with trifluoroacetic acid (2 mL). The solution was stirred for 1 hour at room temperature. The mixture was concentrated under reduced pressure. The crude product was purified by ion exchange chromatography, using a SCX column. The residue was loaded onto the column in methanol and washed with methanol. The desired product was eluted from the column using 2M ammonia in methanol and pure fractions were evaporated to dryness to afford 4-amino-N-(1-(4-chlorophenyl)-2-hydroxyethyl)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidine-4-carboxamide (111 mg, quant.) as a colourless crystalline solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe crude product was purified by ion exchange chromatography
  3. washwashed with methanol
  4. washThe desired product was eluted from the column
  5. customwere evaporated to dryness

Sources & evidence

ORD record
ord-d913fc3b0a8945c488e9c0cb35945747
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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