Triethylamine → Tert-butyl 3-(2-(3-(trifluoromethyl)-1,6-naphthyridin-5-ylamino)acetamido)azetidine-1-carboxylate

HRID 1896937Notes

Reaction equation

Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:6]=[N:7]2.[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.O>[F:13][C:12]([F:15])([F:14])[C:5]1[CH:6]=[N:7][C:8]2[C:3]([CH:4]=1)=[C:2]([NH: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])[N:11]=[CH:10][CH:9]=2

Participants

Conditions

Temperature: 120 °C

Procedure

Into a 10 mL round-bottom flask, was placed a solution of 5-chloro-3-(trifluoromethyl)-1,6-naphthyridine (as prepared in the previous step, 23.3 mg, 0.10 mmol, 1.00 equiv) in diglyme (3 mL), tert-butyl 3-(2-aminoacetamido)azetidine-1-carboxylate (prepared as described in Example 1, Step E) (27 mg, 0.12 mmol, 1.20 equiv) and triethylamine (30 mg, 0.30 mmol, 3.00 equiv). The reaction mixture was stirred overnight at 120° C. The resulting mixture was diluted with 20 mL of H2O. The resulting solution was extracted with 3×20 mL of dichloromethane. The combined organic layers dried (Na2SO4) and concentrated under vacuum. The title compound was obtained as a gray solid.

Workup

customInto a 10 mL round-bottom flask, was placed
extractionThe resulting solution was extracted with 3×20 mL of dichloromethane
dry with materialThe combined organic layers dried (Na2SO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-e6e292bb85f141738ecdb4cbb2ec58be
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518969B2

Reaction notes

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