Methanol → HCID 59255285, compound

HRID 78266Notes

Reaction equation

CO.[NH2:3][C:4]1[C:9]([C:10]2[O:14][N:13]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=3)[CH:11]=2)=[CH:8][CH:7]=[C:6]([NH2:23])[N:5]=1.[OH-].[Na+].[Cl:26][C:27]1[CH:32]=[N:31][CH:30]=[C:29](Cl)[N:28]=1>CN(C)C=O>[Cl:26][C:27]1[N:28]=[C:29]([O:22][C:19]2[CH:20]=[CH:21][C:16]([CH2:15][C:12]3[CH:11]=[C:10]([C:9]4[C:4]([NH2:3])=[N:5][C:6]([NH2:23])=[CH:7][CH:8]=4)[O:14][N:13]=3)=[CH:17][CH:18]=2)[CH:30]=[N:31][CH:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a methanol (1.5 mL) solution of 4-(5-(2,6-diamino-pyridin-3-yl)-isoxazol-3-ylmethyl)-phenol (50 mg, 0.18 mmol) described in Manufacturing Example 18-1-1 was added a 2 N sodium hydroxide solution (89 μL), which was concentrated under a reduced pressure. 2,6-Dichloropyrazine (28 mg, 0.19 mmol) and N,N-dimethylformamide (0.75 mL) were added to the residue, which was stirred for 10 minutes at 100° C. The reaction solution was partitioned into ethyl acetate and water. The organic layer was separated and concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1, then ethyl acetate) to obtain the title compound (47 mg, 67%).

Workup

concentrationwas concentrated under a reduced pressure
customThe reaction solution was partitioned into ethyl acetate and water
customThe organic layer was separated
concentrationconcentrated under a reduced pressure
customThe residue was purified by NH silica gel column chromatography (heptane

Sources & evidence

ORD record: ord-620c7d65510540cda0e3fcc74919e324
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841327B2

Reaction notes

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