Diisopropylethylamine → HCID 44200991, compound

HRID 2061172Notes

Reaction equation

HRID 2061172 reaction equation
[OH:1][C:2]1([C:5]([OH:7])=O)[CH2:4][CH2:3]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:41][N:42]1[C:51]2[C:46](=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=2)[CH:45]=[C:44]([C:53]2[CH:54]=[C:55]([NH:60]/[C:61](/[NH2:64])=[N:62]/O)[CH:56]=[CH:57][C:58]=2[CH3:59])[C:43]1=[O:65]>CN(C=O)C>[OH:1][C:2]1([C:5]2[O:7][N:62]=[C:61]([NH:60][C:55]3[CH:56]=[CH:57][C:58]([CH3:59])=[C:53]([C:44]4[C:43](=[O:65])[N:42]([CH3:41])[C:51]5[C:46]([CH:45]=4)=[CH:47][N:48]=[C:49]([CH3:52])[CH:50]=5)[CH:54]=3)[N:64]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27331601-Hydroxy-1-cyclopropanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178422078HCID 178422078, compound2×

Product 1

HCID 44200991HCID 44200991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-hydroxycyclopropanecarboxylic acid (6 mg, 0.06 mmol) in DMF (1 mL) were added DIPEA (31 μL, 0.18 mmol) and HATU (23 mg, 0.06 mmol). After stirring at rt for 15 min, 17 (20 mg, 0.06 mmol) was added as a solution in DMF (0.5 mL). The reaction was stirred at rt until complete consumption of 17 was determined by LC/MS and then heated at 100° C. for 1 h. Subsequently the reaction was cooled to rt, filtered and purified by preparative LC/MS to give 3-(5-(5-(1-hydroxycyclopropyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A57). MS m/z 404.4 (M+1).

Workup

  1. temperatureheated at 100° C. for 1 h
  2. temperatureSubsequently the reaction was cooled to rt
  3. filtrationfiltered
  4. custompurified by preparative LC/MS

Sources & evidence

ORD record
ord-656945f68f8944d09946bc869a3ed49c
Source dataset
uspto-grants-2012_10
Patent number
US08278452B2

Reaction notes

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