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Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86636281, compound

HRID 541894
Notes
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Reaction equation

HRID 541894 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.[CH3:64][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].[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]([N:9]2[CH2:10][CH2:11][CH:12]([CH2:15][C:16]([NH:86][C:78]3[CH:79]=[CH:80][C:81]4[NH:82][C:83]5[N:84]=[C:68]([NH:69][C:70]6[CH:71]=[N:72][CH:73]=[C:74]([CH:87]=6)[CH2:75][CH2:76][C:77]=3[CH:85]=4)[N:67]=[CH:66][C:65]=5[CH3:64])=[O:18])[CH2:13][CH2:14]2)=[O:8])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 866362826-Methyl-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)

Product 1

HCID 86636281HCID 86636281, compound
Yield 19%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

A solution of {1-[(5-methylisoxazol-3-yl)carbonyl]piperidin-4-yl}acetic acid (4.8 mg, 0.019 mmol) (prepared in Example C49, step I), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (19 mg, 0.050 mmol) in N,N-dimethylformamide (0.2 mL) and N,N-diisopropylethylamine (7.6 uL) was stirred for 15 minutes. A solution of 6-methyl-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) (6.0 mg, 0.019 mmol) (prepared in Example C29, step C) in N,N-dimethylformamide (0.1 mL) and was added to the previous solution and was stirred overnight. The reaction mixture was purified by preparative HPLC (pH 2) to give the desired product (0.5 mg, 19%). LCMS for C30H33N8O3 (M+H)+: m/z=553.2. 1H NMR (300 MHz, DMSO-d6): δ 9.83 (s, 1H), 9.38 (s, 1H), 9.34 (s, 1H), 8.52 (s, 1H), 8.19 (s, 1H), 8.12 (s, 1H), 7.90 (s, 1H), 7.62 (d, J=2.4 Hz, 1H), 7.28 (d, J=8.7 Hz, 1H), 7.00 (dd, J=8.3, 2.2 Hz, 1H), 6.41 (dd, J=8.1, 0.8 Hz, 1H), 4.42 (m, 4H), 3.86 (m, 4H), 2.90-3.10 (m, 6H), 2.10-2.30 (m, 4H), 2.66 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-c49ae7ea39c54816917f100a98f32747
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871753B2

Reaction notes

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