Diisopropylethylamine → HCID 178446224, compound

HRID 1947259Notes

Reaction equation

HRID 1947259 reaction equation
Cl.Cl.[CH:3]1([NH:9][C:10]2[C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:13]([CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])[C:12](=[O:25])[N:11]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[I:49][C:50]1[CH:51]=[C:52]([CH:55]=[CH:56][CH:57]=1)[CH:53]=O>ClCCCl>[CH:3]1([NH:9][C:10]2[C:14]3([CH2:15][CH2:16][N:17]([CH2:53][C:52]4[CH:55]=[CH:56][CH:57]=[C:50]([I:49])[CH:51]=4)[CH2:18][CH2:19]3)[N:13]([CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])[C:12](=[O:25])[N:11]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2526103-IodobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178446226HCID 178446226, compound

Product 1

HCID 178446224HCID 178446224, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 4-(cyclohexylamino)-1-pent-4-en-1-yl-1,3,8-triazaspiro[4.5]dec-3-en-2-one dihydrochloride (1 g, 2.56 mmol, intermediate I.1.c.1) in DCE (16 mL), was added Hunig's base (0.67 mL, 1.42 mmol), sodium triacetoxyborohydride (0.25 g, 1.18 mmol) and 3-iodo-benzaldehyde (329 mg, 3.83 mmol) in DCE (0.5 mL) dropwise. The reaction mixture was stirred at rt for 18 h, quenched with aq NaHCO3, extracted twice with EtOAc, washed with brine, concentrated in vacuo and purified flash chromatography (silica gel, EtOAc) to provide the desired product LRMS (M+1)=535.

Workup

  1. customquenched with aq NaHCO3
  2. extractionextracted twice with EtOAc
  3. washwashed with brine
  4. concentrationconcentrated in vacuo
  5. custompurified flash chromatography (silica gel, EtOAc)

Sources & evidence

ORD record
ord-d891350166ae4cccb1feffecee9d85bb
Source dataset
uspto-grants-2013_03
Patent number
US08399473B2

Reaction notes

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