Isobutyraldehyde → HCID 136128391, compound

HRID 220875Notes

Reaction equation

HRID 220875 reaction equation
[CH:1](=O)[CH:2]([CH3:4])[CH3:3].Cl.[CH3:7][N:8]1[C:17]2[NH:16][C:15]3[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:14]=3[N:13]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH:35]4[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]4)=[C:27]([CH3:41])[CH:26]=3)=[O:24])[CH2:12][C:11]=2[CH:10]=[N:9]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>[CH3:7][N:8]1[C:17]2[NH:16][C:15]3[CH:18]=[C:19]([CH3:22])[CH:20]=[CH:21][C:14]=3[N:13]([C:23]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][CH:35]4[CH2:36][CH2:37][N:38]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:39][CH2:40]4)=[C:27]([CH3:41])[CH:26]=3)=[O:24])[CH2:12][C:11]=2[CH:10]=[N:9]1

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136346638HCID 136346638, compound

Product 1

HCID 136128391HCID 136128391, 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 (3,6-dimethyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulen-9-yl)-[3-methyl-4-(3-piperidin-4-yl-propoxy)-phenyl]-methanone hydrochloride (2.6 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]+=530.5

Workup

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

Sources & evidence

ORD record
ord-bbb8fc78a5f3451bbcf90393fea7126a
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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