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

HRID 564566Notes

Reaction equation

HRID 564566 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:22])[S:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([OH:18])=O)(=[O:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.[NH2:23][CH2:24][C:25]1[C:30]([CH2:31][CH3:32])=[N:29][C:28]2[N:33]([CH2:36][CH3:37])[N:34]=[CH:35][C:27]=2[C:26]=1[NH:38][CH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]([CH3:22])[S:10]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=2)[C:16]([NH:23][CH2:24][C:25]2[C:26]([NH:38][CH:39]3[CH2:40][CH2:41][O:42][CH2:43][CH2:44]3)=[C:27]3[CH:35]=[N:34][N:33]([CH2:36][CH3:37])[C:28]3=[N:29][C:30]=2[CH2:31][CH3:32])=[O:18])(=[O:11])=[O:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578132513-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 578132803-{[[(3-Bromophenyl)methyl](methyl)amino]sulfonyl}-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamideYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{[[(3-bromophenyl)methyl](methyl)amino]sulfonyl}benzoic acid (150 mg, 0.390 mmol) in DCM 7.8 mL) was added 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (133 mg, 0.390 mmol), HBTU (163 mg, 0.429 mmol), and TEA (0.163 mL, 1.171 mmol). This mixture was stirred at room temperature for 2 h. The reaction mixture was washed with H2O (2×3 mL), dried over Na2SO4, filtered, and concentrated. The crude product was further purified by CombiFlash flash chromatograph to afford the title compound (0.2453 mg, 94%). LC-MS m/z 669 (M+H)+.

Workup

  1. washThe reaction mixture was washed with H2O (2×3 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was further purified by CombiFlash flash chromatograph

Sources & evidence

ORD record
ord-ebdc86d4ab434836ad8d87f20645401b
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…