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

HRID 1530535Notes

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 eluting with EtOAc/petroleum ether (1:1) to give N-Methoxy-N-methyl-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-13-carboxamide (800 mg, 50% yield) as a yellow solid. LCMS (ESI) m/z: 383.3 [M+H+].

Workup

customAfter being purged with CO three times
filtrationThe solid was filtered off
concentrationthe filtrate was concentrated
custompurified by silica gel chromatography
washeluting with EtOAc/petroleum ether (1:1)

Sources & evidence

ORD record: ord-3efa812b63484728967e0bd021e96f40
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090628B2

Reaction notes

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