HCID 67034111, compound → HCID 178423425, compound

HRID 539042Notes

Reaction equation

HRID 539042 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:29]=[CH:28][N:27](COCC[Si](C)(C)C)[N:26]=4)=[CH:21][C:20]=3[CH3:38])=[C:12]2[N:11]=1)([CH3:3])[CH3:2].C([C@H]1COC(=O)N1C1C=CN2N=CC(C3C=CC(C4N(COCC[Si](C)(C)C)N=CN=4)=CC=3C)=C2N=1)(C)C>>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:24]=[CH:23][C:22]([C:25]4[N:29]=[CH:28][NH:27][N:26]=4)=[CH:21][C:20]=3[CH3:38])=[C:12]2[N:11]=1)([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 67034111HCID 67034111, compoundHCID 68088739HCID 68088739, compound

Product 1

HCID 178423425HCID 178423425, compoundYield 80%

Procedure

(4S)-4-isopropyl-3-(3-(2-methyl-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.250 g, 80%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (4S)-4-isopropyl-3-(3-(2-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one and (4S)-4-isopropyl-3-(3-(2-methyl-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.414 g, 0.776 mmol), to produce a yellow solid. LCMS (APCI+) m/z 404.6 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 11.07 (broad s, 1H), 8.61 (d, J=7.8 Hz, 1H), 8.22 (m, 2H), 8.03 (d, J=7.8 Hz, 1H), 7.99 (s, 1H), 7.88 (d, J=7.7 Hz, 1H), 7.72 (d, J=8.1 Hz, 1H), 4.84-4.80 (m, 1H), 4.38-4.30 (m, 2H), 2.72-2.64 (m, 1H), 2.51 (s, 3H), 0.94 (d, J=7.0 Hz, 3H), 0.88 (d, J=6.8 Hz, 3H).

Workup

  1. customto produce a yellow solid

Sources & evidence

ORD record
ord-92ec8ae2956645069e070edb4e3a7cf0
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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