Diisopropylethylamine → HCID 117859551, compound

HRID 1486344Notes

Reaction equation

HRID 1486344 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15](O)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=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.Cl.[F:59][C:60]([F:69])([F:68])[CH:61]1[CH2:66][CH:65]([NH2:67])[CH2:64][CH2:63][NH:62]1>CN(C=O)C.C(#N)C.O>[F:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:2]([F:1])[C:3]=1[CH2:4][O:5][C:6]1[N:11]2[N:12]=[C:13]([CH3:18])[C:14]([C:15]([NH:67][CH:65]3[CH2:64][CH2:63][NH:62][CH:61]([C:60]([F:69])([F:59])[F:68])[CH2:66]3)=[O:16])=[C:10]2[CH:9]=[C:8]([CH3:19])[CH:7]=1

Participants

8

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 90232292HCID 90232292, compoundHCID 117859510HCID 117859510, compound

Product 1

HCID 117859551HCID 117859551, compoundYield 26.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 57 mg 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (0.171 mmol) from Example 4A, 72 mg of HATU (0.188 mmol) and 0.179 ml (1.025 mmol) of N,N-diisopropylethylamine in 1.1 ml of DMF was stirred at RT for 20 min. Subsequently, 42 mg (0.205 mmol) of 2-(trifluoromethyl)piperidine-4-amine hydrochloride (Example 36A) were added and the mixture was stirred at RT overnight. The reaction mixture was admixed with water and acetonitrile and purified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.05% formic acid). 22 mg of the target compound were obtained (27% of theory).

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. custompurified by means of preparative HPLC (RP18 column, eluent:acetonitrile/water gradient with addition of 0.05% formic acid)

Sources & evidence

ORD record
ord-eb95fac030bd41e3b65d141b388ee37e
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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