Triethylamine → HCID 25225864, compound

HRID 1958548Notes

Reaction equation

[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[CH:9][CH:10]=2)[NH:5][CH:4]=[C:3]1[C:12]([OH:14])=O.[C:15]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][C:27]=1[NH2:28])[NH:24][CH:23]=[CH:22]2)([CH3:18])([CH3:17])[CH3:16].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:15]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][C:27]=1[NH:28][C:12]([C:3]1[C:2](=[O:1])[C:11]3[C:6](=[CH:7][N:8]=[CH:9][CH:10]=3)[NH:5][CH:4]=1)=[O:14])[NH:24][CH:23]=[CH:22]2)([CH3:18])([CH3:16])[CH3:17]

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylic acid (48 mg, 0.25 mmol), 5-tert-butyl-1H-indol-6-amine (48 mg, 0.25 mmol) in DMF (1 mL) was added HATU (106 mg, 0.28 mmol), followed by triethylamine (106 μL, 0.76 mmol) and the reaction mixture was heated at 80° C. for 16 h. The reaction mixture was then purified by reverse phase HPLC 10-99% ACN in water to give N-(5-tert-butyl-1H-indol-6-yl)-4-oxo-1,4-dihydro-1,7-naphthyridine-3-carboxamide. MS m/z: 361.5 [M+H]+

Workup

customThe reaction mixture was then purified by reverse phase HPLC 10-99% ACN in water

Sources & evidence

ORD record: ord-71a6ac60ffdf4df99a5237fdc3929661
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08410132B2

Reaction notes

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