Trifluoroacetic acid → HCID 86608324, compound

HRID 2233979Notes

Reaction equation

[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15]([C:18]2[N:23]=[C:22]([O:24][CH2:25][CH:26]3[CH2:30][O:29]C(C)(C)[O:27]3)[N:21]=[C:20]([C:33]([NH:35][O:36][CH3:37])=[O:34])[CH:19]=2)[CH2:14][CH2:13]1)=[O:10].C(O)(C(F)(F)F)=O.[OH-].[NH4+]>C1COCC1.O>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][CH:12]1[CH2:13][CH2:14][N:15]([C:18]2[N:23]=[C:22]([O:24][CH2:25][CH:26]([OH:27])[CH2:30][OH:29])[N:21]=[C:20]([C:33]([NH:35][O:36][CH3:37])=[O:34])[CH:19]=2)[CH2:16][CH2:17]1)=[O:10]

Participants

Conditions

Temperature: 0 °C

Procedure

6-(4-{[(3,4-Dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)-2-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-N-methoxypyrimidine-4-carboxamide (Example 313; 0.60 g, 1.08 mmol) was dissolved in THF/water (4:1; 2.5 ml) and cooled to 0° C. TFA (0.1 ml) was added to the solution which was then slowly warmed to room temperature and stirred overnight. The mixture was neutralized with concentrated ammonium hydroxide and the THF was removed in vacuo. The mixture was diluted with water (4 ml), extracted with DCM, and the organic layers dried over magnesium sulfate. The mixture was concentrated in vacuo and crude product was purified by reverse phase chromatography eluting with acetonitrile/water (0.1% TFA) (33 mg).

Workup

temperaturewas then slowly warmed to room temperature
customthe THF was removed in vacuo
additionThe mixture was diluted with water (4 ml)
extractionextracted with DCM
dry with materialthe organic layers dried over magnesium sulfate
concentrationThe mixture was concentrated in vacuo and crude product
customwas purified by reverse phase chromatography
washeluting with acetonitrile/water (0.1% TFA) (33 mg)

Sources & evidence

ORD record: ord-72ce73cc5e5d4c15b2e38e40d9eeb7ed
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

Loading…