HCID 67033917, compound → HCID 178422941, compound

HRID 538996Notes

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)=[C:21]([CH3:38])[CH:20]=3)=[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)=C(C)C=3)=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)=[C:21]([CH3:38])[CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 67033917HCID 67033917, compound

HCID 67034104HCID 67034104, compound

Product 1

HCID 178422941HCID 178422941, compoundYield 64%

Procedure

(S)-4-isopropyl-3-(3-(3-methyl-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one (0.138 g, 64%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (S)-4-isopropyl-3-(3-(3-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 (S)-4-isopropyl-3-(3-(3-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 (0.285 g, 0.534 mmol), to produce a yellow solid. LCMS (APCI+) m/z 404.6 [M+H]+; 1H-NMR (400 MHz, CDCl3) δ 11.40 (broad s, 1H), 8.60 (d, J=7.8 Hz, 1H), 8.41 (s, 1H), 8.22 (s, 1H), 8.05 (d, J=7.8 Hz, 1H), 7.94 (s, 1H), 7.87 (d, J=8.0 Hz, 1H), 7.81 (d, J=8.2 Hz, 1H), 4.97-4.93 (m, 1H), 4.48-4.38 (m, 2H), 2.94-2.87 (m, 1H), 2.65 (s, 3H), 1.07 (d, J=7.0 Hz, 3H), 0.93 (d, J=6.8 Hz, 3H).

Workup

customto produce a yellow solid

Sources & evidence

ORD record: ord-a263eb069c81454590ce7630830d012d
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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