HCID 67033328, compound → HCID 178448162, compound

HRID 539043Notes

Reaction equation

[Cl: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[C@@H:34]([CH:35]([CH3:37])[CH3:36])[CH2:33][O:32][C:31]4=[O:38])=[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.ClC1C=C(C2C=NN3C=CC(N4[C@@H](C(C)C)COC4=O)=NC=23)C=CC=1C1N(COCC[Si](C)(C)C)N=CN=1>>[Cl: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[C@@H:34]([CH:35]([CH3:36])[CH3:37])[CH2:33][O:32][C:31]4=[O:38])=[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 67033328HCID 67033328, compound

HCID 67034736HCID 67034736, compound

Product 1

HCID 178448162HCID 178448162, compoundYield 25%

Procedure

(S)-3-(3-(3-Chloro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (0.051 g, 25%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (S)-3-(3-(3-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 (S)-3-(3-(3-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 (0.270 g, 0.487 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), 8.83 (s, 1H), 8.67 (s, 1H), 8.39 (m, 1H), 8.09 (m, 1H), 7.95-7.82 (m, 2H), 4.96-4.92 (m, 1H), 4.56-4.50 (m, 2H), 2.80-2.76 (m, 1H), 1.07 (d, J=7.1 Hz, 3H), 0.86 (d, J=6.8 Hz, 3H).

Workup

customto produce a yellow solid

Sources & evidence

ORD record: ord-b11268d675664cc98979110da246aee2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

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