Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-3-{[({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzamide

HRID 564651Notes

Reaction equation

HRID 564651 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][NH:22][S:23]([C:26]4[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=4)[C:29](O)=[O:30])(=[O:25])=[O:24])[CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:4][CH2:3]1.Cl.[NH2:36][CH2:37][C:38]1[C:43]([CH2:44][CH3:45])=[N:42][C:41]2[N:46]([CH2:49][CH3:50])[N:47]=[CH:48][C:40]=2[C:39]=1[NH:51][CH:52]1[CH2:57][CH2:56][O:55][CH2:54][CH2:53]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[CH2:49]([N:46]1[C:41]2=[N:42][C:43]([CH2:44][CH3:45])=[C:38]([CH2:37][NH:36][C:29](=[O:30])[C:28]3[CH:32]=[CH:33][CH:34]=[C:26]([S:23]([NH:22][CH2:21][C:17]4[CH:16]=[C:15]([C:11]5[CH:12]=[CH:13][CH:14]=[C:9]([CH2:8][CH:5]6[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]6)[CH:10]=5)[CH:20]=[CH:19][CH:18]=4)(=[O:25])=[O:24])[CH:27]=3)[C:39]([NH:51][CH:52]3[CH2:53][CH2:54][O:55][CH2:56][CH2:57]3)=[C:40]2[CH:48]=[N:47]1)[CH3:50]

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578134563-{[({3'-[(1-Methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzoic AcidHCID 670055525-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine hydrochloride

Product 1

HCID 57813351N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-3-{[({3'-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzamideYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-{[({3′-[(1-methyl-4-piperidinyl)methyl]-3-biphenylyl}methyl)amino]sulfonyl}benzoic acid (0.086 g, 0.102 mmol) in THF (1 mL) was added 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine hydrochloride (0.042 g, 0.122 mmol), HBTU (0.048 g, 0.133 mmol), and TEA (0.036 mL, 0.255 mmol) and the reaction was stirred at room temperature for 18 h. The reaction mixture was concentrated on Glas-Col evaporator, purified using a Gilson HPLC (with 0.1% TFA), concentrated, basified with amino cartridge to afford 0.0458 g (59%) of the title compound. LC-MS m/z 764 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated on Glas-Col evaporator
  2. custompurified
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1d549dab7fc24161b5bb3fb45d6b91a3
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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