Trifluoroacetic acid → HCID 67200202, compound

HRID 509974Notes

Reaction equation

C(OC(=O)[N:7]([C:18]1[N:23]=[CH:22][C:21]([CH:24]([C:26]2[C:34]3[C:29](=[N:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=3)[N:28]([S:37]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:27]=2)O)=[CH:20][N:19]=1)[CH2:8][C:9]1[C:10]([O:16][CH3:17])=[N:11][CH:12]=[C:13]([F:15])[CH:14]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:40]1([S:37]([N:28]2[C:29]3=[N:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=[C:34]3[C:26]([CH2:24][C:21]3[CH:22]=[N:23][C:18]([NH:7][CH2:8][C:9]4[C:10]([O:16][CH3:17])=[N:11][CH:12]=[C:13]([F:15])[CH:14]=4)=[N:19][CH:20]=3)=[CH:27]2)(=[O:39])=[O:38])[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To {5-[(1-benzenesulfonyl-5-methoxy-1H-pyrrolo[2,3-b]pyridin-3-yl)-hydroxy-methyl]-pyrimidin-2-yl}-(5-fluoro-2-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (124, 1 equivalent) in 10.0 mL of acetonitrile, triethylsilane (15.6 equivalents) and trifluoroacetic acid (16.9 equivalents) are added. The reaction is heated at 80° C. for 2 hours, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered and the filtrate concentrated under vacuum to provide the desired compound, which is used in the next step without further purification.

Workup

extractionextracted with ethyl acetate
dry with materialThe organic layer is dried over sodium sulfate
filtrationfiltered
concentrationthe filtrate concentrated under vacuum

Sources & evidence

ORD record: ord-8581bd83d614468f8d989709420824f9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096593B2

Reaction notes

Loading…