Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86671464, compound

HRID 1530542Notes

Reaction equation

Br[C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=2)=[CH:10]3)=[CH:4][CH:3]=1.Cl.[CH3:25][NH:26][O:27][CH3:28].CC1(C)C2[C:51](=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)[O:50]C2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>CC([O-])=O.CC([O-])=O.[Pd+2].C1(C)C=CC=CC=1>[CH3:28][O:27][N:26]([CH3:25])[C:51]([C:2]1[CH:15]=[C:14]2[C:5]([O:6][CH2:7][CH2:8][N:9]3[C:13]2=[N:12][C:11]([C:16]2[N:20]([CH:21]([CH3:23])[CH3:22])[N:19]=[CH:18][N:17]=2)=[CH:10]3)=[CH:4][CH:3]=1)=[O:50]

Participants

Conditions

Temperature: 80 °C

Procedure

To a round bottom flask was added 13-bromo-4-[1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]-9-oxa-3,6-diazatricyclo[8.4.0.02,6]tetradeca1(14),2,4,10,12-pentaene (1.6 g, 4.3 mmol), N,O-dimethylhydroxylamine hydrochloride (0.62 g, 6.4 mmol), Pd(OAc)2 (95 mg, 0.43 mmol), Xantphos (0.49 g, 0.85 mmol), TEA (1.3 g, 13 mmol) and toluene (20 mL). After being purged with CO three times, the mixture was heated at 80° C. overnight. The solid was filtered off. The filtrate was concentrated and purified by silica gel chromatography using 50% EtOAc in petroleum ether as eluant to give the desired product (800 mg, 50% yield) as a yellow solid. LCMS m/z [M+H]+ 383.3

Workup

customAfter being purged with CO three times
filtrationThe solid was filtered off
concentrationThe filtrate was concentrated
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-38868c1a768b42c28f05dd514bd2cc1c
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

Loading…