Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 57813532, compound

HRID 564652Notes

Reaction equation

HRID 564652 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=O)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].Cl.Cl.[CH3:36][N:37]1[CH:42]2[CH2:43][CH2:44][CH:38]1[CH2:39][CH:40]([CH2:45][C:46]1[CH:47]=[C:48]([C:52]3[CH:57]=[CH:56][CH:55]=[C:54]([CH2:58][NH2:59])[CH:53]=3)[CH:49]=[CH:50][CH:51]=1)[CH2:41]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CS(C)=O>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([NH:59][CH2:58][C:54]4[CH:53]=[C:52]([C:48]5[CH:49]=[CH:50][CH:51]=[C:46]([CH2:45][CH:40]6[CH2:39][CH:38]7[N:37]([CH3:36])[CH:42]([CH2:43][CH2:44]7)[CH2:41]6)[CH:47]=5)[CH:57]=[CH:56][CH:55]=4)=[O:28])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidHCID 67006469HCID 67006469, compound

Product 1

HCID 57813532HCID 57813532, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (0.045 g, 0.1 mmol) in DMSO (0.5 mL) was added 1-{3′-[(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)methyl]-3-biphenylyl}methanamine dihydrochloride (0.047 g, 0.12 mmol), HBTU (0.054 g, 0.15 mmol), and TEA (0.042 mL, 0.3 mmol) and the reaction was stirred at room temperature for 16 h. The reaction mixture was purified using a Gilson HPLC (with 0.1% TFA), concentrated, basified with amino cartridge to afford 0.0409 g (52%) of the title compound. LC-MS m/z 754 (M+H)+.

Workup

  1. customThe reaction mixture was purified
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-ed244d292345429f8ca2d04ec40a19ca
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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