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Triethylamine → HCID 25225864, compound

HRID 1931331
Notes
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Reaction equation

HRID 1931331 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 451174204-Oxo-1,4-dihydro-1,7-naphthyridine-3-carboxylic acidHCID 57470208HCID 57470208, compound

Product 1

HCID 25225864HCID 25225864, compound

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

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

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

Sources & evidence

ORD record
ord-295d17433ce74967bf0d8d94611c25c1
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188283B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes