HCID 68088754, compound → HCID 178519090, compound

HRID 539095Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[N:41]5[CH2:46][CH2:45][N:44](C(OC(C)(C)C)=O)[CH2:43][CH2:42]5)[CH2:33][O:32][C:31]4=[O:54])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=1.FC1C=C(C2C=NN3C=CC(N4C(C5C=CC=CC=5N5CCN(C(OC(C)(C)C)=O)CC5)COC4=O)=NC=23)C=CC=1C1N(COCC[Si](C)(C)C)N=CN=1>>[F:1][C:2]1[CH:3]=[C:4]([C:21]2[CH:22]=[N:23][N:24]3[CH:29]=[CH:28][C:27]([N:30]4[CH:34]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=5[N:41]5[CH2:42][CH2:43][NH:44][CH2:45][CH2:46]5)[CH2:33][O:32][C:31]4=[O:54])=[N:26][C:25]=23)[CH:5]=[CH:6][C:7]=1[C:8]1[N:12]=[CH:11][NH:10][N:9]=1

Participants

Reactant 2

HCID 68088754HCID 68088754, compound

HCID 68088996HCID 68088996, compound

Product 1

HCID 178519090HCID 178519090, compoundYield 43%

Procedure

3-(3-(3-fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-(2-(piperazin-1-yl)phenyl)oxazolidin-2-one (36 mg, 43%) was prepared by the procedure described in Example 1, Step 9, using a mixture of tert-butyl 4-(2-(3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-2-oxooxazolidin-4-yl)phenyl)piperazine-1-carboxylate and tert-butyl 4-(2-(3-(3-(3-fluoro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-2-oxooxazolidin-4-yl)phenyl)piperazine-1-carboxylate. LCMS (APCI+) m/z 526.1 [M+H]+.

Sources & evidence

ORD record: ord-2656203026744c98b21e504ce88afd39
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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