HCID 67033445, compound → HCID 178448160, compound

HRID 539022Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][N:10](COCC[Si](C)(C)C)[N:9]=2)[CH:5]=[CH:4][C:3]=1[C:21]1[CH:22]=[N:23][N:24]2[CH:29]=[CH:28][C:27]([N:30]3[C@@H:34]([CH:35]([CH3:37])[CH3:36])[CH2:33][O:32][C:31]3=[O:38])=[N:26][C:25]=12.ClC1C=C(C2N(COCC[Si](C)(C)C)N=CN=2)C=CC=1C1C=NN2C=CC(N3[C@@H](C(C)C)COC3=O)=NC=12>>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[N:12]=[CH:11][NH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[C:21]1[CH:22]=[N:23][N:24]2[CH:29]=[CH:28][C:27]([N:30]3[C@@H:34]([CH:35]([CH3:36])[CH3:37])[CH2:33][O:32][C:31]3=[O:38])=[N:26][C:25]=12

Participants

Reactant 2

HCID 67033445HCID 67033445, compound

HCID 67033567HCID 67033567, compound

Product 1

HCID 178448160HCID 178448160, compoundYield 65%

Procedure

(4S)-3-(3-(2-Chloro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (0.078 g, 65%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (4S)-3-(3-(2-chloro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one and (4S)-3-(3-(2-chloro-4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-5-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (0.158 g, 0.285 mmol), to produce a yellow solid. LCMS (APCI+) m/z 424.6 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ 14.21 (broad s, 1H), 9.13 (d, J=7.8 Hz, 1H), 8.64 (s, 1H), 8.29 (s, 1H), 8.15 (s, 1H), 8.08 (m, 1H), 8.00 (d×d, J=8.2, 1.5 Hz, 1H), 7.93 (d, J=7.8 Hz, 1H), 4.85-4.81 (m, 1H), 4.45-4.44 (m, 2H), 2.70-2.66 (m, 1H), 0.95 (d, J=7.1 Hz, 3H), 0.84 (d, J=7.0 Hz, 3H).

Workup

customto produce a yellow solid

Sources & evidence

ORD record: ord-f3a86b25a1c04814a47b8a6215ba2976
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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