Triethylamine → HCID 59255510, compound

HRID 1694180Notes

Reaction equation

[C:1]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:2].[F:10][C:11]1[CH:16]=[C:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:14]=[CH:13][C:12]=1[CH2:25][C:26](Cl)=[N:27][OH:28].C(N(CC)CC)C>O1CCCC1>[F:10][C:11]1[CH:16]=[C:15]([CH2:17][O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:14]=[CH:13][C:12]=1[CH2:25][C:26]1[CH:2]=[C:1]([C:3]2[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=2)[O:28][N:27]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a tetrahydrofuran (3 mL) solution of the 3-ethynyl-pyridin-2-ylamine (38.4 mg, 0.325 mmol) described in Manufacturing Example 1-2-3 and (2-fluoro-4-(pyridin-2-yloxymethyl)-phenyl)acetohydroximoyl chloride (150 mg, 0.509 mmol) described in Manufacturing Example 204-1-8 was added triethylamine (97.2 μL, 0.697 mmol), which was stirred for 2 hours at 60° C. The mixture was cooled to room temperature and partitioned into ethyl acetate and water. The organic layer was separated, washed with water, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4 to 1:2, then 1:1) to obtain the title compound (46 mg, 24%).

Workup

temperatureThe mixture was cooled to room temperature
custompartitioned into ethyl acetate and water
customThe organic layer was separated
washwashed with water
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThe filtrate was concentrated under a reduced pressure
customthe residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record: ord-472b7677298444988d1011291924e19a
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158657B2

Reaction notes

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