Propanal → HCID 136128402, compound

HRID 220884Notes

Reaction equation

HRID 220884 reaction equation
[CH:1](=O)[CH2:2][CH3:3].[CH3:5][N:6]1[C:15]2[NH:14][C:13]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]=3[N:11]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([N:33]4[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]4)=[O:32])=[C:25]([CH3:39])[CH:24]=3)=[O:22])[CH2:10][C:9]=2[CH:8]=[N:7]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCN(C(C)C)C(C)C.CN(C=O)C>[CH3:5][N:6]1[C:15]2[NH:14][C:13]3[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:12]=3[N:11]([C:21]([C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH2:30][C:31]([N:33]4[CH2:38][CH2:37][N:36]([CH2:1][CH2:2][CH3:3])[CH2:35][CH2:34]4)=[O:32])=[C:25]([CH3:39])[CH:24]=3)=[O:22])[CH2:10][C:9]=2[CH:8]=[N:7]1

Participants

7

Reactant 3

HCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 136128407HCID 136128407, compound

Product 1

HCID 136128402HCID 136128402, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolvent2×HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A solution of propionaldehyde (0.29 mg, 0.005 mmol) in 1,2-dichloroethane (0.05 ml) was added to a solution of 3-[4-(3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-2-methyl-phenyl]-1-piperazin-1-yl-propan-1-one (2.36 mg, 0.005 mmol) in 1,2-dichloroethane (0.05 ml) and DIEA (0.0026 ml). The mixture was stirred at room temperature for 1 h then a solution of sodium triacetoxyborohydride (1.59 mg, 0.0075 mmol) in DMF (0.05 ml) was added. The mixture was stirred for 20 h at room temperature then solvents were removed in vacuo to yield the title compound. (ESI)+: [M+H]+=515.5

Workup

  1. stirringThe mixture was stirred for 20 h at room temperature
  2. customsolvents were removed in vacuo

Sources & evidence

ORD record
ord-8d97611dddbc4e7f85fac4abeb390aee
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

Loading…