Triethylamine → HCID 68004015, compound

HRID 1896949Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[CH:5]=[N:4][N:3]=1.[NH2:16][CH2:17][C:18]([NH:20][CH:21]1[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]1)=[O:19].C(N(CC)CC)C>COCCOCCOC>[F:13][C:12]([F:15])([F:14])[C:9]1[C:10]([NH:16][CH2:17][C:18]([NH:20][CH:21]2[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:22]2)=[O:19])=[C:11]2[C:6](=[CH:7][CH:8]=1)[CH:5]=[N:4][N:3]=[CH:2]2

Participants

Conditions

Temperature: 100 °C

Procedure

Into a 50 mL round-bottom flask, was placed a solution of 1-chloro-7-(trifluoromethyl)phthalazine (prepared as described in the previous step, 1.5 g, 6.47 mmol, 1.00 equiv) in 2-methoxyethyl ether (10 mL), tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (prepared as described in Example 1, Step E) (1.5 g, 6.55 mmol, 1.22 equiv) and triethylamine (1.95 g, 19.31 mmol, 2.99 equiv). The reaction mixture was stirred overnight at 100° C. in an oil bath. The reaction progress was monitored by LCMS. The resulting mixture was concentrated under vacuum. The residue was purified by chromatography over a silica gel column with CH3CN:H2O (3:1). The title compound was obtained as a white solid.

Workup

customInto a 50 mL round-bottom flask, was placed
concentrationThe resulting mixture was concentrated under vacuum
customThe residue was purified by chromatography over a silica gel column with CH3CN:H2O (3:1)

Sources & evidence

ORD record: ord-3ccc744dd60f459e994394eb81cb4b79
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

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