Diisopropylethylamine → HCID 23146362, compound

HRID 2378022Notes

Reaction equation

HRID 2378022 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.N1C[CH2:21][CH2:20][CH2:19][CH:18]1[CH2:23][C:24]1N=C2C=CC=CN2N=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.[F:50][P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[CH3:66][C:67]1[S:68][CH:69]=[C:70]([C:72]([OH:74])=O)[N:71]=1>CN(C=O)C>[F:50][C:18]1[CH:19]=[CH:20][C:21]([C:69]2[S:68][C:67]([CH3:66])=[N:71][C:70]=2[C:72]([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:74])=[CH:24][CH:23]=1

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 2847282-Methyl-1,3-thiazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 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 (API30 ): 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-e482890902b04a31896fed2e7dc790c5
Source dataset
uspto-grants-2008_12
Patent number
US07470710B2

Reaction notes

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