Acetic Acid → HCID 57424595, compound

HRID 1093232Notes

Reaction equation

HRID 1093232 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:17]=[C:16]3[N:18]([CH:21]4[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]4)[N:19]=[CH:20][C:15]3=[C:14]([N:28]3[CH2:34][CH:33]4[O:35][CH:30]([CH2:31][CH2:32]4)[CH2:29]3)[N:13]=2)=[CH:8][CH:7]=1)=[O:4].[CH3:36][N:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:17]=[C:16]3[N:18]([CH:21]4[CH2:22][CH2:23][CH:24]([N:40]5[CH2:41][CH2:42][N:37]([CH3:36])[CH2:38][CH2:39]5)[CH2:25][CH2:26]4)[N:19]=[CH:20][C:15]3=[C:14]([N:28]3[CH2:29][CH:30]4[O:35][CH:33]([CH2:32][CH2:31]4)[CH2:34]3)[N:13]=2)=[CH:10][CH:11]=1)=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 25260758HCID 25260758, compound

Product 1

HCID 57424595HCID 57424595, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-methyl-3-{4-[4-(8-oxa-3-azabicyclo[3.2.1]oct-3-yl)-1-(4-oxocyclohexyl)-1H-pyrazolo[3,4-d]pyrimidin-6-yl]phenyl}urea (65 mg) in DCE (2.0 mL) was added excess N-methylpiperizine, acetic acid (0.012 mL) and excess sodium triacetoxyborohydride. The mixture was stirred at room temperature overnight. The reaction was quenched with water and the organics were separated and concentrated under nitrogen and purified by Gilson HPLC to give the desired product (56 mg) MS m/z=560.3 (M+H).

Workup

  1. customThe reaction was quenched with water
  2. customthe organics were separated
  3. concentrationconcentrated under nitrogen
  4. custompurified by Gilson HPLC

Sources & evidence

ORD record
ord-d83e7bb284bc48d482d824cb15bc17e4
Source dataset
uspto-grants-2012_03
Patent number
US08129371B2

Reaction notes

Loading…