Diisopropylethylamine → HCID 71576484, compound

HRID 930046Notes

Reaction equation

HRID 930046 reaction equation
C(N(CC)C(C)C)(C)C.[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:21]=[C:20]([C:29]([OH:31])=O)[CH:19]=2)[CH:14]=[C:15]([F:17])[CH:16]=1.Cl.[NH:33]1[CH:37]=[CH:36][NH:35][C:34]1=O.CN(C([O:46]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.C(#N)C.CN(C=O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:21]=[C:20]([C:29]([N:33]3[CH2:37][C:36](=[O:46])[NH:35][CH2:34]3)=[O:31])[CH:19]=2)[CH:14]=[C:15]([F:17])[CH:16]=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 66687731HCID 66687731, compoundHCID 89602575HCID 89602575, compound

Product 1

HCID 71576484HCID 71576484, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.12 ml (0.71 mmol) of N,N-diisopropylethylamine as well as 0.5 ml of DMF are added to a solution of 75 mg (0.24 mmol) of the compound of Example 20A, 32 mg (0.26 mmol) of 4-imidazolinone-hydrochloride, and 126 mg (0.33 mmol) of HATU in 1 ml of THF, and the mixture that is obtained is stirred for 16 hours at room temperature. The reaction mixture is diluted with acetonitrile, filtered over a Millipore spray filter, and separated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient). 71 mg (78% of theory) of the title compound is obtained.

Workup

  1. customthe mixture that is obtained
  2. filtrationfiltered over a Millipore spray
  3. filtrationfilter
  4. customseparated by means of preparative HPLC (mobile solvent: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-0372d39e359e428888b7e7cf0b2c5330
Source dataset
uspto-grants-2016_03
Patent number
US09296720B2

Reaction notes

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