Triethylamine → HCID 57580519, compound

HRID 1692425Notes

Reaction equation

HRID 1692425 reaction equation
[CH:1]1([C:4]2[C:9]([C:10](N3CCC(N4CCCC4)CC3)=[O:11])=[C:8]([CH3:23])[N:7]=[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:34])([F:33])[F:32])[CH:25]=3)[N:5]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.Cl.Cl.[OH:68][CH2:69][C@H:70]1[N:74]([CH:75]2[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]2)[CH2:73][C@H:72]([NH:81][C:82](=[O:84])[CH3:83])[CH2:71]1>CN(C=O)C>[CH:1]1([C:4]2[C:9]([C:10]([N:78]3[CH2:77][CH2:76][CH:75]([N:74]4[C@H:70]([CH2:69][OH:68])[CH2:71][C@@H:72]([NH:81][C:82](=[O:84])[CH3:83])[CH2:73]4)[CH2:80][CH2:79]3)=[O:11])=[C:8]([CH3:23])[N:7]=[C:6]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]([F:33])([F:34])[F:32])[CH:25]=3)[N:5]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57580529HCID 57580529, compoundHCID 66901559HCID 66901559, compound2×

Product 1

HCID 57580519HCID 57580519, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In analogy to the procedure described for intermediate 2,4-cyclopropyl-6-methyl-2-(3-trifluoromethoxy-phenyl)-pyrimidine-5-carboxylic acid (example 36) was reacted with HATU, triethylamine and N-((3R,5S)-5-hydroxymethyl-1-piperidin-4-yl-pyrrolidin-3-yl)-acetamide dihydrochloride (intermediate 8) in DMF. Subsequent purification by preparative HPLC afforded the title compound as a gum. MS: 562.3 (MH+).

Workup

  1. customSubsequent purification by preparative HPLC

Sources & evidence

ORD record
ord-14eca246b3c8486bb6c82fdc442c1408
Source dataset
uspto-grants-2012_04
Patent number
US08153805B2

Reaction notes

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