Trifluoroacetic acid → HCID 53946319, compound

HRID 251504Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH:17]C(=O)OC(C)(C)C)=[N:15][CH:16]=3)=[CH:9][N:8]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]2[C:10]([C:11]3[CH:12]=[CH:13][C:14]([NH2:17])=[N:15][CH:16]=3)=[CH:9][N:8]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of tert-butyl N-[5-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-pyridyl]carbamate (0.13 g, 0.315 mmol) in dichloromethane (5.5 ml) was cooled to 0° C. then treated with trifluoroacetic acid (0.6 ml). The solution was stirred at 0° C. for 5 minutes then warmed to ambient temperature and stirred for a further 18 hours. The solvents were evaporated under reduced pressure then the residue was partitioned between dichloromethane (30 ml) and saturated aqueous sodium bicarbonate (10 ml). The organic solution was dried over magnesium sulfate filtered and the filtrate evaporated under reduced pressure to give 5-(4-chloro-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-pyridinamine (92 mg): RP-HPLC (Hypersil HyPurity Elite C18, 5 μm, 200 A, 250×4.6 mm; 25-100% acetonitrile-0.1 M ammonium acetate over 25 min, 1 ml/min) tr=10.73 min; MS: MH+314.

Workup

temperaturethen warmed to ambient temperature
stirringstirred for a further 18 hours
customThe solvents were evaporated under reduced pressure
customthe residue was partitioned between dichloromethane (30 ml) and saturated aqueous sodium bicarbonate (10 ml)
dry with materialThe organic solution was dried over magnesium sulfate
filtrationfiltered
customthe filtrate evaporated under reduced pressure

Sources & evidence

ORD record: ord-808bc21ea2d44a55bc92fb3c4f5adf7d
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863444B2

Reaction notes

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