Formaldehyde → HCID 89662849, compound

HRID 1479081Notes

Reaction equation

HRID 1479081 reaction equation
[CH:1](O)=O.[NH:4]1[CH2:7][CH:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([N:17]2[CH2:31][C:20]3=[C:21]4[N:26]([N:27]=[C:19]3[CH2:18]2)[C:25]([CH3:28])=[C:24]([Cl:29])[C:23]([CH3:30])=[N:22]4)=[O:16])[CH2:5]1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[Cl:29][C:24]1[C:23]([CH3:30])=[N:22][C:21]2[N:26]([N:27]=[C:19]3[CH2:18][N:17]([C:15]([C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[O:8][CH:6]4[CH2:7][N:4]([CH3:1])[CH2:5]4)=[O:16])[CH2:31][C:20]3=2)[C:25]=1[CH3:28]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 122512305HCID 122512305, compound

Product 1

HCID 89662849HCID 89662849, compoundYield 21.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of Example 104 (112 mg; 0.25 mmol; 1 eq.), paraformaldehyde (68 mg; 0.76 mmol; 3.00 eq.) and sodium triacetoxyborohydride (107 mg; 0.50 mmol; 2 eq.) in DCE (5 mL) was stirred at reflux for 2 hours. 1M NaOH was added and extracted several times with EtOAc. The combined organics were dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (22 mg, 21%) as a white solid. 1H NMR (CDCl3) δ 7.40-7.33 (m, 2H), 7.11-7.05 (m, 1H), 6.73-6.69 (m, 1H), 5.03-5.01 (m, 2H), 4.97-4.89 (m, 1H), 4.61-4.60 (m, 2H), 4.16-4.10 (m, 2H), 3.34-3.28 (m, 2H), 2.91 (s, 2H), 2.85 (s, 1H), 2.69 (s, 1H), 2.62 (s, 2H), 2.51 (s, 3H). HPLC (max plot) 98%, Rt 1.92 min. UPLC/MS: (MS+) 412.4 ([M+H]+).

Workup

  1. temperatureat reflux for 2 hours
  2. extractionextracted several times with EtOAc
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification by mass

Sources & evidence

ORD record
ord-cca507df5c4546be8ed03695055e4f64
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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