6-(4-(5-(Hydroxymethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one → 6-(4-(5-(Aminomethyl)-1H-1,2,4-triazol-3-YL)phenyl)-1-(2-(tetrahydro-2H-pyran-4-YL)ethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388145Notes

Reaction equation

HRID 388145 reaction equation
Cl[CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]4[N:20]([CH2:24][CH2:25][CH:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[C:21](=[O:23])[NH:22][C:17]4=[N:16][CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1.OCC1NN=C(C2C=CC(C3N=C4N(CCC5CCOCC5)C(=O)NC4=NC=3)=CC=2)[N:35]=1>S(Cl)(Cl)=O>[NH2:35][CH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:19]=[C:18]4[N:20]([CH2:24][CH2:25][CH:26]5[CH2:31][CH2:30][O:29][CH2:28][CH2:27]5)[C:21](=[O:23])[NH:22][C:17]4=[N:16][CH:15]=3)=[CH:10][CH:9]=2)[N:4]=1

Participants

4

Reactant 2

HCID 666999366-(4-(5-(Hydroxymethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneHCID 666999726-(4-(5-(Chloromethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

Product 1

HCID 249860426-(4-(5-(Aminomethyl)-1H-1,2,4-triazol-3-YL)phenyl)-1-(2-(tetrahydro-2H-pyran-4-YL)ethyl)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneYield 81%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

6-(4-(5-(Chloromethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 6-(4-(5-(Hydroxymethyl)-1H-1,2,4-triazol-3-yl)phenyl)-1-(2-(tetrahydro-2H-pyran-4-yl)ethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.130 g, 0.31 mmol) in thionyl chloride (2 mL) was stirred in a sealed tube at 80° C. for 1 h. The cooled reaction solvent was removed under reduced pressure. The resulting material was dried under vacuum at 50° C. to give the desired product (0.110 g, 81%) as a white solid. MS (ESI) m/z 440.0[M+1]+.

Workup

  1. customThe cooled reaction solvent
  2. customwas removed under reduced pressure
  3. customThe resulting material was dried under vacuum at 50° C.

Sources & evidence

ORD record
ord-caeb9a41e75045e0835b61dcb2b854dc
Source dataset
uspto-grants-2013_02
Patent number
US08372976B2

Reaction notes

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