Hexanal → HCID 57554577, compound

HRID 551951Notes

Reaction equation

HRID 551951 reaction equation
[CH3:1][C:2]1([CH3:33])[O:7][C:6]2[CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]#[C:21][C:22]4[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=4)=[CH:16][CH:15]=3)=[CH:11][C:5]=2[C:4](=[O:32])[O:3]1.[CH:34](=O)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]>>[CH2:34]([N:12]([CH2:13][C:14]1[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)=[CH:18][CH:19]=1)[C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([CH3:33])([CH3:1])[O:3][C:4](=[O:32])[C:5]=2[CH:11]=1)[CH2:35][CH2:36][CH2:37][CH2:38][CH3:39]

Participants

3

Reactant 2

HCID 6184HexanalHCID 57554502HCID 57554502, compound

Product 1

HCID 57554577HCID 57554577, compoundYield 78%

Procedure

The title compound was prepared following procedure described in Example 32, step c) from 2,2-dimethyl-6-[(4-{[4-(trifluoromethyl)phenyl]ethynyl}benzyl)amino]-4H-1,3-benzodioxin-4-one (427 mg; 0.95 mmol) and hexanal (Aldrich, 170 μl; 1.42 mmol) to give 560 mg of crude. Purification by flash chromatography on silica gel (EtOAc/c-Hexe 5:90 then 10:90) gave 395 mg (78%) of the title compound as a brown powder. HPLC, Rt: 6.21 min (purity: 68.5%). 1H NMR (CDCl3) δ: 7.59 (brs, 4H), 7.47 (m, 2H), 7.30.(m 3H), 6.76-6.83 (m, 2H), 4.50 (s, 2H), 3.38 (m, 2H), 1.68 (s, 6H), 1.61 (m, 2H), 1.28 (m, 6H), 0.86 (m, 3H).

Workup

  1. customThe title compound was prepared following procedure
  2. customto give 560 mg of crude
  3. customPurification by flash chromatography on silica gel (EtOAc/c-Hexe 5:90

Sources & evidence

ORD record
ord-c441f34425df46d49abf7607b7d70b2f
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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