Ammonium Chloride → HCID 90403910, compound

HRID 1049261Notes

Reaction equation

[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([N:15]3[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]3)[CH:10]=2)=[CH:6][CH:5]=[C:4]([N+:21]([O-])=O)[N:3]=1.[NH4+].[Cl-]>CO.C(Cl)Cl.[Zn]>[CH3:1][C:2]1[N:3]=[C:4]([NH2:21])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([N:15]2[CH:19]=[C:18]([CH3:20])[N:17]=[CH:16]2)[CH:10]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A suspension of 2-methyl-3-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.50 g, 4.82 mmol) and NH4Cl (6.00 g, 112 mmol) in MeOH (30 mL) was treated with zinc dust (3.00 g, 45.9 mmol) and heated at 40° C. for 3 h. The mixture was diluted with DCM, the solids removed via filtration, washed with MeOH/DCM and the filtrate concentrated to dryness. The residue was treated with DCM, the solids again removed via filtration and the filtrate concentrated to dryness to afford 6-methyl-5-((2-(4-methyl-1H-imidazol-1-yl)pyridin-4-yl)oxy)pyridin-2-amine (1.02 g, 75%). 1H NMR (400 MHz, DMSO-d6): δ 8.37 (d, J=1.4 Hz, 1H), 8.26 (d, J=5.8 Hz, 1H), 7.61 (t, J=1.3 Hz, 1H), 7.28 (d, J=2.2 Hz, 1H), 7.20 (d, J=8.7 Hz, 1H), 6.60 (dd, J=5.8, 2.2 Hz, 1H), 6.34 (d, J=8.7 Hz, 1H), 5.97 (s, 2H), 2.13 (s, 3H), 2.07 (s, 3H); MS (ESI) m/z: 282.1 (M+H+).

Workup

customthe solids removed via filtration
washwashed with MeOH/DCM
concentrationthe filtrate concentrated to dryness
additionThe residue was treated with DCM
customthe solids again removed via filtration
concentrationthe filtrate concentrated to dryness

Sources & evidence

ORD record: ord-acbd60739235408f9e0ce38fb6a185c1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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