Trifluoroacetic acid → {6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1775190Notes

Reaction equation

HRID 1775190 reaction equation
C(OC(=O)[N:7]([CH2:25][C:26]1[CH:27]=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=1)[C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:16]2[C:24]3[CH:23]=[N:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)=[O:15])=[CH:10][N:9]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:33][O:32][C:29]1[N:28]=[CH:27][C:26]([CH2:25][NH:7][C:8]2[N:9]=[CH:10][C:11]([C:14]([C:16]3[C:24]4[CH:23]=[N:22][CH:21]=[N:20][C:19]=4[NH:18][CH:17]=3)=[O:15])=[CH:12][CH:13]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57963060(6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl ester

Product 1

HCID 57963230{6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanoneYield 9.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (73, 66 mg, 0.14 mmol) in 5 mL of dichloromethane, trifluoroacetic acid (0.5 mL, 6.0 mmol) was added. The reaction was stirred at room temperature for 4 hours, then concentrated under vacuum, and combined with aqueous saturated sodium bicarbonate and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate adsorbed onto silica. This was purified by silica gel column chromatography eluting with methanol and dichloromethane. Appropriate fractions were combined, the solvents removed under vacuum, and the resulting solid washed with hexanes and ethyl acetate, with sonicating. The solid was collected by filtration to provide the desired compound as a white solid (P-0008, 4.8 mg). MS (ESI) [M+H+]+=360.9.

Workup

  1. concentrationconcentrated under vacuum
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customThis was purified by silica gel column chromatography
  5. washeluting with methanol and dichloromethane
  6. customthe solvents removed under vacuum
  7. washthe resulting solid washed with hexanes and ethyl acetate
  8. customwith sonicating
  9. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-4b166e05ff874a11bd7ad1759ebc928b
Source dataset
uspto-grants-2016_02
Patent number
US09260437B2

Reaction notes

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