Formaldehyde → HCID 58980857, compound

HRID 1181340Notes

Reaction equation

HRID 1181340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH:27][CH2:28][C:29]5[CH:34]=[CH:33][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:31][CH:30]=5)=[C:20]([O:38][CH3:39])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH2:40]=O>C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]([CH2:28][C:29]5[CH:30]=[CH:31][C:32]([CH:35]([CH3:37])[CH3:36])=[CH:33][CH:34]=5)[CH3:40])=[C:20]([O:38][CH3:39])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 58980866HCID 58980866, compound

Product 1

HCID 58980857HCID 58980857, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The product from Example H17 (12 mg) was dissolved in 37% formaldehyde (1 mL) and 88% formic acid (1 mL). The solution was refluxed for 2 h. The solvents were removed by rotary evaporation and the product was purified by silica gel column chromatography giving the title compound (10 mg, 81%). 1H NMR (CDCl3) δ 1.25 (6H, d), 2.40 (3H, s), 2.90 (2H, m), 3.65 (2H, m), 3.90 (3H, s), 4.21 (2H, m), 6.91-7.00 (3H, m), 7.19-7.34 (4H, m), 7.46 (2H, d, J=8.4 Hz). 7.55 (1H, s), 7.68 (2H, d, J=8.6 Hz), 8.15 (1H, s). LCMS m/z=574 (m+H+).

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. customThe solvents were removed by rotary evaporation
  3. customthe product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-541a3237fe7f4e5b9734c7948b44a8bf
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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