Diisopropylethylamine → HCID 117859714, compound

HRID 1486346Notes

Reaction equation

HRID 1486346 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.Cl.[CH3:60][S:61][CH2:62][CH2:63][CH:64]([NH2:67])[CH2:65][NH2:66]>CN(C=O)C.C(#N)C.O>[NH2:67][CH:64]([CH2:63][CH2:62][S:61][CH3:60])[CH2:65][NH:66][C:15]([C:14]1[C:13]([CH3:18])=[N:12][N:11]2[C:6]([O:5][CH2:4][C:3]3[C:2]([F:1])=[CH:23][CH:22]=[CH:21][C:20]=3[F:24])=[CH:7][C:8]([CH3:19])=[CH:9][C:10]=12)=[O:16]

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 71758022HCID 71758022, compoundHCID 117859510HCID 117859510, compound

Product 1

HCID 117859714HCID 117859714, compoundYield 75.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 70 mg of 7-[(2,6-difluorobenzyl)oxy]-2,5-dimethylpyrazolo[1,5-a]pyridine-3-carboxylic acid (75% purity, 0.118 mmol) from Example 4A, 66 mg of HATU (0.174 mmol) and 0.083 ml (0.474 mmol) of N,N-diisopropylethylamine in 0.7 ml of DMF was stirred at RT for 10 min. This reaction mixture was added to a solution of 53 mg (0.236 mmol) of rac-4-(methylsulphanyl)butane-1,2-diamine dihydrochloride in 0.14 ml of DMF at 0° C. and the mixture was stirred for 60 min. 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). 40 mg of the target compound were obtained (54% of theory).

Workup

  1. stirringthe mixture was stirred for 60 min
  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-f9b46802d8fe422fbe8303d41aceafdb
Source dataset
uspto-grants-2016_08
Patent number
US09422285B2

Reaction notes

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