Isobutyraldehyde → HCID 136128404, compound

HRID 220807Notes

Reaction equation

HRID 220807 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]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]([C:22]([CH:24]3[CH2:29][CH2:28][CH:27]([CH2:30][NH:31][C:32]([CH:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)=[O:33])[CH2:26][CH2:25]3)=[O:23])[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]=[CH:19][CH:20]=[CH:21][C:14]=3[N:13]([C:22]([CH:24]3[CH2:25][CH2:26][CH:27]([CH2:30][NH:31][C:32]([CH:34]4[CH2:35][CH2:36][N:37]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:38][CH2:39]4)=[O:33])[CH2:28][CH2:29]3)=[O:23])[CH2:12][C:11]=2[CH:10]=[N:9]1

Participants

7

Reactant 3

HCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 136346635HCID 136346635, compound

Product 1

HCID 136128404HCID 136128404, 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 piperidine-4-carboxylic acid [4-(3-methyl-4,10-dihydro-3H-2,3,4,9-tetraaza-benzo[f]azulene-9-carbonyl)-cyclohexylmethyl]-amide hydrochloride (Compound number 238) (2.43 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]+=507.4

Workup

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

Sources & evidence

ORD record
ord-13059a1ef5c646e2b1d0098758a0756b
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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