Isobutyric Acid → HCID 57725639, compound

HRID 1988436Notes

Reaction equation

HRID 1988436 reaction equation
[C:1]([OH:6])(=O)[CH:2]([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:40][NH:41][C:42](=[O:66])[C:43]1[CH:48]=[C:47]([O:49][C:50]2[CH:65]=[CH:64][C:53]3[N:54]=[C:55]([NH:57][C@H:58]4[CH2:63][CH2:62][CH2:61][NH:60][CH2:59]4)[S:56][C:52]=3[CH:51]=2)[CH:46]=[CH:45][N:44]=1>CC(N(C)C)=O>[C:1]([N:60]1[CH2:61][CH2:62][CH2:63][C@H:58]([NH:57][C:55]2[S:56][C:52]3[CH:51]=[C:50]([O:49][C:47]4[CH:46]=[CH:45][N:44]=[C:43]([C:42]([NH:41][CH3:40])=[O:66])[CH:48]=4)[CH:65]=[CH:64][C:53]=3[N:54]=2)[CH2:59]1)(=[O:6])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 6590Isobutyric AcidHCID 81531Diisopropylethylamine2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57725452HCID 57725452, compound

Product 1

HCID 57725639HCID 57725639, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To the reaction solution of isobutyric acid (4 μl, 40 μmol), HATU (15 mg, 40 μmol) and DIEA (14 μL, 80 μmol) in 400 μL of DMA was added (S)—N-methyl-4-(2-(piperidin-3-ylamino)benzo[d]thiazol-6-yloxy)picolinamide (13 mg, 30 μmol) and DIPEA (6 μL, 30 μmol). The reaction solution was stirred at room temperature for 16 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give (S)-4-(2-(1-isobutyrylpiperidin-3-ylamino)benzo[d]thiazol-6-yloxy)-N-methylpicolinamide (6.8 mg, 15 μmol) as white powder. ES/MS m/z 454.2 (MH+).

Workup

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f86697e11795413da5e1b8bcab87add7
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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