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Diisopropylethylamine → HCID 178459998, compound

HRID 931398
Notes
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Reaction equation

HRID 931398 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH3:17])[C:12](=[CH2:16])[C:13]([OH:15])=O)=[CH:7][CH:6]=1)=[O:4].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:42][C:43]1[C:48]([Br:49])=[CH:47][CH:46]=[CH:45][N+:44]=1[O-:50].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Br:49][C:48]1[C:43]([NH:42][C:13](=[O:15])[C:12](=[CH2:16])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:10][CH:9]=2)[CH3:17])=[N+:44]([O-:50])[CH:45]=[CH:46][CH:47]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 900107323-(4-(Methoxycarbonyl)phenyl)-2-methylenebutanoic acidHCID 178507188HCID 178507188, compound

Product 1

HCID 178459998HCID 178459998, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 3-(4-(methoxycarbonyl)phenyl)-2-methylenebutanoic acid (1.0 g, 4.2 mmol), HATU (1.9 g, 5.1 mmol), 2-amino-3-bromopyridine 1-oxide (0.88 g, 4.6 mmol) and diisopropyl ethylamine (2.22 mL, 12.5 mmol) in anhydrous DMF (10 mL) was stirred at 23° C. for 1 h, then concentrated. The residue was partitioned between ethyl acetate and brine (2×). The combined organic layers were dried over anhydrous sodium sulfate, and concentrated. The residue was triturated with acetonitrile (20 mL). The solid was filtered and dried under vacuum to give the title compound. MS: m/z=406.0 (M+1).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and brine (2×)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with acetonitrile (20 mL)
  6. filtrationThe solid was filtered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-c914242757004a578e545691f262b725
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296750B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes