HCID 67033386, compound → HCID 178448161, compound

HRID 539024Notes

Reaction equation

[F: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.FC1C=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>>[F: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 67033386HCID 67033386, compound

HCID 67034254HCID 67034254, compound

Product 1

HCID 178448161HCID 178448161, compoundYield 48%

Procedure

(4S)-3-(3-(2-Fluoro-4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one (0.186 g, 48%) was prepared by the procedure described in Example 1, Step 9, using a mixture of (4S)-3-(3-(2-fluoro-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-fluoro-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 (0.507 g, 0.943 mmol), to produce a yellow solid. LCMS (APCI+) m/z 408.6 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ 14.27 (broad s, 1H), 9.16 (d, J=7.8 Hz, 1H), 8.57-8.52 (m, 3H), 7.96-7.85 (m, 3H), 4.97-4.93 (m, 1H), 4.52-4.48 (m, 2H), 2.78-2.71 (m, 1H), 1.05 (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-34eb17a5481945d6a1f74fde6c77fbee
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865726B2

Reaction notes

Loading…