Diisopropylethylamine → HCID 23146362, compound

HRID 1367029Notes

Reaction equation

HRID 1367029 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][C:8]1[N:16]=[C:11]2[CH2:12][CH2:13][CH2:14][CH2:15][N:10]2[N:9]=1.N1CCCCC1CC1N=C2C=CC=CN2N=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[F:66][C:67]1[CH:72]=[CH:71][C:70]([C:73]2[S:77][C:76]([CH3:78])=[N:75][C:74]=2[C:79](O)=[O:80])=[CH:69][CH:68]=1>CN(C=O)C>[F:66][C:67]1[CH:68]=[CH:69][C:70]([C:73]2[S:77][C:76]([CH3:78])=[N:75][C:74]=2[C:79]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]2[CH2:7][C:8]2[N:16]=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[O:80])=[CH:71][CH:72]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 223241255-(4-Fluorophenyl)-2-methyl-1,3-thiazole-4-carboxylic acidHCID 23146301HCID 23146301, compoundHCID 23146330HCID 23146330, compound

Product 1

HCID 23146362HCID 23146362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of 2-piperidin-2-ylmethyl-5,6,7,8-tetrahydro-[1,2,4]-triazolo[1,5-a]pyridine and 2-piperidin-2-ylmethyl-[1,2,4]-triazolo[1,5-a]pyridine, D34 (0.220 g) was treated with HATU (0.380 g), N,N-diisopropylethylamine (1.0 ml) and 5-(4-fluorophenyl)-2-methylthiazole-4-carboxylic acid (0.240 g) in dry DMF, according to the procedure described in Example 60. The crude product was chromatographed (silica gel, 4% methanol-diethyl ether) to afford 1-[5-(4-fluoro-phenyl)-2-methylthiazol-4-yl]-1-(2-[1,2,4]-triazolo[1,5-a]pyridin-2-ylmethylpiperidin-1-yl)-methanone as a colourless foam (0.070 g) (Mass spectrum (API+): found 436 (MH+): C23H22FN5OS requires 435). Continued elution (10% methanol-diethyl ether) afforded 1-[5-(4-fluoro-phenyl)-2-methyl-thiazol-4-yl]-1-[2-(5,6,7,8-tetrahydro-[1,2,4]-triazolo[1,5-a]pyridin-2-ylmethyl)-piperidin-1-yl]-methanone as a colourless foam (0.230 g) (Mass spectrum (API+): found 440 (MH+): C23H26FN5OS requires 439).

Workup

  1. customThe crude product was chromatographed (silica gel, 4% methanol-diethyl ether)

Sources & evidence

ORD record
ord-37316e0753524752a44717ac5472bb53
Source dataset
uspto-grants-2011_02
Patent number
US07893090B2

Reaction notes

Loading…