1,2-Dichloroethane → 3-(Chloromethyl)-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide

HRID 564519Notes

Reaction equation

HRID 564519 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[Cl:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28](O)=[O:29].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[Cl:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=1)[C:28]([NH:1][CH2:2][C:3]1[C:4]([NH:16][CH:17]2[CH2:18][CH2:19][O:20][CH2:21][CH2:22]2)=[C:5]2[CH:13]=[N:12][N:11]([CH2:14][CH3:15])[C:6]2=[N:7][C:8]=1[CH2:9][CH3:10])=[O:29]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2417523-(Chloromethyl)benzoic acidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 578134963-(Chloromethyl)-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamideYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridine-4-amine (0.303 g, 1.0 mmol) in CH2Cl2 (10 mL) was added 3-(chloromethyl)benzoic acid (0.188 g, 1.1 mmol), EDC (0.288 g, 1.5 mmol), HOBt (0.0135 g, 0.1 mmol), and Et3N (0.141 mL, 1.0 mmol). This mixture was stirred at room temperature for 1 h, then washed with H2O (1 mL) and purified by CombiFlash chromatograph to afford the title compound 0.285 g (63%). LC-MS m/z 456 (M+H)+.

Workup

  1. washwashed with H2O (1 mL)
  2. custompurified by CombiFlash chromatograph

Sources & evidence

ORD record
ord-2d488a4b5f94426d9b01282063f3ffd3
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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