Diisopropylethylamine → HCID 67107393, compound

HRID 1623836Notes

Reaction equation

HRID 1623836 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]1[CH:12]=[C:13]([NH2:17])[CH:14]=[N:15][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Br:42][C:43]1[CH:44]=[CH:45][C:46]([O:52][CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=2)=[C:47]([CH:51]=1)[C:48](O)=[O:49]>CN(C)C=O>[Br:42][C:43]1[CH:44]=[CH:45][C:46]([O:52][CH2:53][C:54]2[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=2)=[C:47]([CH:51]=1)[C:48]([NH:17][C:13]1[CH:14]=[N:15][CH:16]=[C:11]([F:10])[CH:12]=1)=[O:49]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5744505-Fluoro-3-pyridinamineHCID 24613572-(Benzyloxy)-5-bromobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 67107393HCID 67107393, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (0.28 ml, 1.63 mmol), 5-fluoro-3-pyridinamine (73.0 mg, 0.65 mmol) and HATU (371 mg, 0.98 mmol) were added to a solution of 5-bromo-2-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 5; 200 mg, 0.651 mmol) in N,N-dimethylformamide (50 ml) at room temperature. The mixture was stirred at room temperature for 3 hours. The mixture was then purified by chromatography on silica using 0-100% ethyl acetate/hexane. However a number of impurities persisted and the residue was re-purified by MDAP to yield the title compound. 45 mg.

Workup

  1. customThe mixture was then purified by chromatography on silica using 0-100% ethyl acetate/hexane
  2. customthe residue was re-purified by MDAP

Sources & evidence

ORD record
ord-cf283712855e4ee18aad3fc0a46b7d44
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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