Nitrogen → HCID 72704327, compound

HRID 1484524Notes

Reaction equation

[C:1]([O:5]C)(=O)[NH:2][NH2:3].O.[C:8]1(C)C=CC(S(O)(=O)=O)=C[CH:9]=1.N#N.[C:21](OC)(OC)(OC)C.C([O-])(O)=O.[Na+].[NH2:34][C:35]1[CH:36]=[C:37]([CH3:51])[C:38]([O:41][C:42]2[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][CH2:49]C)[CH:43]=2)=[N:39][CH:40]=1>CO>[CH3:8][C:9]1[N:34]([C:35]2[CH:40]=[N:39][C:38]([O:41][C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([CH:48]([CH3:49])[CH3:21])[CH:43]=3)=[C:37]([CH3:51])[CH:36]=2)[C:1](=[O:5])[NH:2][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of methyl carbazate (372 mg, 4.13 mmol) and p-toluenesulfonic acid monohydrate (16 mg, 0.083 mmol) in methanol (12 mL) was purged with N2 and trimethyl orthoacetate (496 mg, 4.12 mmol) was added. The mixture was stirred at 60° C. for 4 hrs and NaHCO3 (7 mg, 0.083 mmol) was added. The solid was filtered off and the filtrate was evaporated to afford an intermediate, which was mixed with 5-amino-3-methyl-2-{[3-(2-methylethyl)phenyl]oxy}-pyridine (Intermediate 26, 200 mg, 0.83 mmol) and heated to 110° C. in a vial for 5 days. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (petroleum ether/ethyl acetate from 1:1 to 1:2) to afford the title compound (30 mg) as a grey solid.

Workup

additionwas added
filtrationThe solid was filtered off
customthe filtrate was evaporated
customto afford an intermediate, which
temperatureheated to 110° C. in a vial for 5 days
customThe solvent was removed under reduced pressure
customthe residue was purified by silica gel chromatography (petroleum ether/ethyl acetate from 1:1 to 1:2)

Sources & evidence

ORD record: ord-e0cffa8084d045919f363c9c9353a522
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422252B2

Reaction notes

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