Isobutyraldehyde → HCID 136128427, compound

HRID 220797Notes

Reaction equation

HRID 220797 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].Cl.[NH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])[CH2:11][CH2:10]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>[CH2:1]([NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([N:17]2[CH2:26][C:25]3[CH:24]=[N:23][N:22]([CH3:27])[C:21]=3[NH:20][C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]2=3)=[O:16])[CH2:11][CH2:10]1)[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136346632HCID 136346632, compound

Product 1

HCID 136128427HCID 136128427, compound

Reagents, catalysts & solvents 3

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

Procedure

A solution of isobutyraldehyde (0.36 mg, 0.005 mmol) in 1,2-dichloroethane (0.05 ml) was added to a solution of (4-Aminomethyl-cyclohexyl)-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-methanone hydro-chloride from Example E10.2 (1.88 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]+=396.4

Workup

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

Sources & evidence

ORD record
ord-1776575dd1d04dfcaafd251c5e22fb85
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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