Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86636284, compound

HRID 541900Notes

Reaction equation

HRID 541900 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.[CH3:26][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].[F:57][C:58]1[CH:59]=[N:60][C:61]2[NH:62][C:63]3[CH:64]=[CH:65][CH:66]=[C:67]([CH:80]=3)[CH2:68][CH2:69][C:70]3[CH:78]=[C:74]([NH:75][C:76]=1[N:77]=2)[CH:73]=[CH:72][C:71]=3[NH2:79]>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:57][C:58]1[CH:59]=[N:60][C:61]2[NH:62][C:63]3[CH:64]=[CH:65][CH:66]=[C:67]([CH:80]=3)[CH2:68][CH2:69][C:70]3[CH:78]=[C:74]([NH:75][C:76]=1[N:77]=2)[CH:73]=[CH:72][C:71]=3[NH:79][C:16](=[O:18])[CH2:15][CH:12]1[CH2:11][CH2:10][N:9]([C:7]([C:4]2[CH:3]=[C:2]([CH2:1][CH3:26])[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 86636286HCID 86636286, compound

Product 1

HCID 86636284HCID 86636284, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of {1-[(5-methylisoxazol-3-yl)carbonyl]piperidin-4-yl}acetic acid (16 mg, 0.063 mmol) (prepared in Example C49, step I), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (65 mg, 0.17 mmol) in N,N-dimethylformamide (0.8 mL) and N,N-diisopropylethylamine (26 μL) was stirred for 15 minutes. A solution of 6-fluoro-2,4,8,22-tetraazatetracyclo[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 bis(trifluoroacetate) (20 mg, 0.06 mmol) in N,N-dimethylformamide (0.3 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 (4 mg, 12%). LCMS for C30H31FN7O3 (M+H)+: m/z=556.2

Workup

  1. customwas stirred for 15 minutes
  2. customThe reaction mixture was purified by preparative HPLC (pH 2)

Sources & evidence

ORD record
ord-8549897cfdbf41b58acb44878e00fcd2
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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