Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86636278, compound

HRID 541891Notes

Reaction equation

HRID 541891 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][C:16]([OH:18])=O)[CH2:11][CH2:10]2)=[O:8])[CH:3]=1.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)ON1C2N=CC=CC=2N=N1.[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].FC(F)(F)C(O)=O.[F:64][C:65]1[CH:66]=[N:67][C:68]2[NH:69][C:70]3[CH:71]=[N:72][CH:73]=[C:74]([CH:87]=3)[CH2:75][CH2:76][C:77]3[CH:85]=[C:81]([NH:82][C:83]=1[N:84]=2)[CH:80]=[CH:79][C:78]=3[NH2:86]>CN(C)C=O.C(N(CC)C(C)C)(C)C>[F:43][C:44]([F:49])([F:48])[C:45]([OH:47])=[O:46].[F:50][C:51]([F:56])([F:55])[C:52]([OH:54])=[O:53].[F:64][C:65]1[CH:66]=[N:67][C:68]2[NH:69][C:70]3[CH:71]=[N:72][CH:73]=[C:74]([CH:87]=3)[CH2:75][CH2:76][C:77]3[CH:85]=[C:81]([NH:82][C:83]=1[N:84]=2)[CH:80]=[CH:79][C:78]=3[NH:86][C:16](=[O:18])[CH2:15][CH:12]1[CH2:11][CH2:10][N:9]([C:7]([C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)=[O:8])[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57962578HCID 57962578, compoundHCID 86636279HCID 86636279, compound

Product 1

HCID 86636278HCID 86636278, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of {1-[(5-methylisoxazol-3-yl)carbonyl]piperidin-4-yl}acetic acid (2.0 mg, 0.0079 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (8.1 mg, 0.021 mmol) in N,N-dimethylformamide (0.1 mL) and N,N-diisopropylethylamine (3.2 uL) was stirred for 15 minutes. A solution of 6-fluoro-2,4,8,18,22-pentaazatetracyclo[14.3.1.1(3,7).1(9,13)]docosa-1(20),3(22),4,6,9(21),10,12,16,18-nonaen-12-amine tris(trifluoroacetate) (2.5 mg, 0.0078 mmol) in N,N-dimethylformamide (0.04 mL) and was added to the previous solution and stirred overnight. The reaction mixture was purified by preparative HPLC (pH 2) to give the desired product (0.5 mg, 14%). LCMS for C29H30FN8O3 (M+H)+: m/z=557.1.

Workup

  1. customThe reaction mixture was purified by preparative HPLC (pH 2)

Sources & evidence

ORD record
ord-2ea144db230942ea8d201f335b5d75bc
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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