4-Aminobenzoic Acid → HCID 57990405, compound

HRID 2381718Notes

Reaction equation

HRID 2381718 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:27]C2CC2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:6]=2[N:7]=1.[NH2:31][C:32]1[CH:40]=[CH:39][C:35]([C:36]([OH:38])=[O:37])=[CH:34][CH:33]=1.C[Si](Cl)(C)C>C(O)CCC>[NH2:27][C:4]1[C:5]2[C:10]([C:11]3[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=3)=[CH:9][NH:8][C:6]=2[N:7]=[C:2]([NH:31][C:32]2[CH:40]=[CH:39][C:35]([C:36]([O:38][CH2:4][CH2:5][CH2:10][CH3:9])=[O:37])=[CH:34][CH:33]=2)[N:3]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 6397ChlorotrimethylsilaneHCID 579903022-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 57990405HCID 57990405, compoundYield 122.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 2-chloro-N-cyclopropyl-5-(pyridin-4-yl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (245 mg, 0.557 mmol), 4-aminobenzoic acid (150 mg, 1.09 mmol) and trimethylsilyl chloride (0.300 mL, 2.37 mmol) in nBuOH (4 mL) was stirred at 135° C. for 24 h. It was concentrated in vacuo. The residue was purified by HPLC to give butyl 4-(4-amino-5-(pyridin-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)benzoate (137 mg).

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-4adc1cf96ce841758a5ab47bf8894d54
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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