Formaldehyde → HCID 56928659, compound

HRID 1772131Notes

Reaction equation

HRID 1772131 reaction equation
[NH:1]1[CH2:4][CH:3]([C:5]2[CH:6]=[CH:7][C:8]([NH:11][C:12]3[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=[C:14]([C:20]4[C:21]([CH2:40][OH:41])=[C:22]([N:26]5[CH2:34][C:33]6[C:28](=[CH:29][CH:30]=[C:31]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH:32]=6)[C:27]5=[O:39])[CH:23]=[CH:24][CH:25]=4)[CH:13]=3)=[N:9][CH:10]=2)[CH2:2]1.C=O.O.[C:45]([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:35]([C:31]1[CH:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[C:27](=[O:39])[N:26]([C:22]1[CH:23]=[CH:24][CH:25]=[C:20]([C:14]3[CH:13]=[C:12]([NH:11][C:8]4[CH:7]=[CH:6][C:5]([CH:3]5[CH2:2][N:1]([CH3:45])[CH2:4]5)=[CH:10][N:9]=4)[C:17](=[O:18])[N:16]([CH3:19])[CH:15]=3)[C:21]=1[CH2:40][OH:41])[CH2:34]2)([CH3:37])([CH3:38])[CH3:36]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 56928658HCID 56928658, compound

Product 1

HCID 56928659HCID 56928659, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent2×

Procedure

A 150-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with 117(72 mg, 0.130 mmol), 37% solution of formaldehyde in water (5 mg, 0.170 mmol) and anhydrous methanol (5 mL). A suspension of sodium cyanoborohydride (25 mg, 0.400 mmol) and anhydrous zinc chloride (27 mg, 0.200 mmol) in anhydrous methanol (2.5 mL) was added, and the reaction was stirred at room temperature for 5 h. After this time, the reaction mixture was concentrated, and 10% aqueous potassium carbonate (5 mL) was added. The resulting suspension was filtered, and the filter cake was washed with water (2 mL). The filter cake was purified by column chromatography to afford a 64% yield (56 mg) of 118 as a white solid: mp 201-202° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.54 (s, 1H), 8.11 (s, 1H), 7.72 (d, 2H, J=8.5 Hz), 7.64 (m, 2H), 7.49 (t, 1H, J=8.0 Hz), 7.44 (d, 1H, J=6.5 Hz), 7.37 (m, 2H), 7.27 (d, 1H, J=8.5 Hz), 4.94 (s, 2H), 4.88 (t, 1H, J=4.5 Hz), 4.34 (d, 2H, J=4.5 Hz), 3.59 (s, 3H), 3.54 (t, 2H, J=7.0 Hz), 3.45 (m, 1H), 3.01 (t, 2H, J=6.5 Hz), 2.24 (s, 3H), 1.36 (s, 9H); MS (ESI+) m/z 564.3 (M+H).

Workup

  1. customA 150-mL single-neck round-bottomed flask equipped with a magnetic stirrer
  2. customwas purged with nitrogen
  3. additionwas added
  4. concentrationAfter this time, the reaction mixture was concentrated
  5. addition10% aqueous potassium carbonate (5 mL) was added
  6. filtrationThe resulting suspension was filtered
  7. washthe filter cake was washed with water (2 mL)
  8. customThe filter cake was purified by column chromatography

Sources & evidence

ORD record
ord-395f26b2ed5046108a36695bca6590f3
Source dataset
uspto-grants-2016_02
Patent number
US09249123B2

Reaction notes

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