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Triethylamine → tert-butyl(1-(4-(1-(dimethylamino)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamate

HRID 1509279
Notes
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Reaction equation

HRID 1509279 reaction equation
Br[C:2]1[N:6]2[C:7]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[C:12]([C:21]4[CH:26]=[CH:25][C:24]([C:27]5([NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)=[N:11][C:8]=3[O:9][CH2:10][C:5]2=[N:4][N:3]=1.Cl.[CH3:40][NH:41][CH3:42].C(N(CC)CC)C>CN1C(=O)CCC1.C(Cl)Cl.O>[C:34]([O:33][C:32](=[O:38])[NH:31][C:27]1([C:24]2[CH:23]=[CH:22][C:21]([C:12]3[C:13]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)=[CH:14][C:7]4[N:6]5[C:2]([N:41]([CH3:42])[CH3:40])=[N:3][N:4]=[C:5]5[CH2:10][O:9][C:8]=4[N:11]=3)=[CH:26][CH:25]=2)[CH2:28][CH2:29][CH2:30]1)([CH3:36])([CH3:37])[CH3:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 89541876HCID 89541876, compound

Product 1

HCID 131734407tert-butyl(1-(4-(1-(dimethylamino)-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutyl)carbamateYield 20.9%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of tert-butyl 1-(4-(1-bromo-8-phenyl-4H-pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]oxazin-7-yl)phenyl)cyclobutylcarbamate (41 mg, 0.071 mmol), dimethylamine hydrochloride (58.2 mg, 0.714 mmol), and triethylamine (0.099 ml, 0.714 mmol) in NMP (1 ml) was heating at 130 degree for 50 min under microwave condition. The mixture was diluted with DCM (8 ml) and water (8 ml). The organic phase was washed with water (8 mlX3) and brine (5 ml). Concentrated and purified by column eluted with MeOH/DCM (0-4%) to give product (8 mg). 1H NMR (500 MHz, CDCl3) 8.15 (s, 1H), 7.15-7.34 (m, 9H), 5.51 (s, 2H), 5.01 (s, 1H), 2.95 (s, 6H), 2.4-2.5 (m, 4H), 2.0-2.15 (m, 1H), 1.75-1.85 (m, 1H), 1.2-1.35 (m, 9H).

Workup

  1. temperaturewas heating at 130 degree for 50 min under microwave condition
  2. washThe organic phase was washed with water (8 mlX3) and brine (5 ml)
  3. concentrationConcentrated
  4. custompurified by column
  5. washeluted with MeOH/DCM (0-4%)

Sources & evidence

ORD record
ord-c2a6de8a0a574d279b37f0388547a89b
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221838B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes