3-Hydroxypyridine → HCID 69201717, compound

HRID 2252242Notes

Reaction equation

O[CH2:2][C:3]1[CH:4]=[C:5]2[C:28](=[CH:29][CH:30]=1)[C:8]1[N:9](COCC[Si](C)(C)C)[N:10]=[C:11]([C:12]3[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=3)[C:7]=1[CH2:6]2.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[OH:66][C:67]1[CH:68]=[N:69][CH:70]=[CH:71][CH:72]=1>C1COCC1>[N:69]1[CH:70]=[CH:71][CH:72]=[C:67]([O:66][CH2:2][C:3]2[CH:4]=[C:5]3[C:28](=[CH:29][CH:30]=2)[C:8]2[NH:9][N:10]=[C:11]([C:12]4[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[N:16][CH:17]=4)[C:7]=2[CH2:6]3)[CH:68]=1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of Example 131A (60.0 mg, 0.143 mmol), di-t-butyl azodicarboxylate (39.6 mg, 0.172 mmol), Ph3P on solid support (3 mmol/g, 57.3 mg, 0.172 mmol), and 3-hydroxypyridine (16.4 mg, 0.172 mmol) in THF (2 mL) was stirred at room temperature overnight. The solid was filtered and the solvent was evaporated. The crude product was treated with HCl (concentrated, 4 drops) and EtOH (4 mL). The mixture was heated in a capped vial at 75° C. for 2 hours. The solvent was evaporated and the residue was purified using reversed-phase HPLC to give the desired product (12.4 mg) as TFA salt. MS (ESI) m/z: 366.0 (M+H)+. 1H NMR (300 MHz, DMSO-D6) δ ppm 4.01 (s, 2H) 5.83 (s, 2H) 7.58 (d, J=7.80 Hz, 1H) 7.74 (m, 1H) 7.80 (s, 1H) 7.93-8.05 (m, 2H) 8.18 (d, J=8.14 Hz, 1H) 8.40 (dd, J=8.14, 2.37 Hz, 1H) 8.62-8.84 (m, 2H) 9.19 (s, 1H) 12.14 (s, 1H).

Workup

filtrationThe solid was filtered
customthe solvent was evaporated
additionThe crude product was treated with HCl (concentrated, 4 drops) and EtOH (4 mL)
customThe solvent was evaporated
customthe residue was purified

Sources & evidence

ORD record: ord-cb41e2791975436d82b629bdaff3c2a3
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07320986B2

Reaction notes

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