Formaldehyde → HCID 10008897, compound

HRID 1374964Notes

Reaction equation

HRID 1374964 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9]([C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[C:20]([C:22](=[O:41])[NH:23][C:24]4[CH:29]=[C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:27]=[C:26]([NH:34][S:35]([CH3:38])(=[O:37])=[O:36])[C:25]=4[O:39][CH3:40])[CH:19]=[CH:18][C:17]=3[CH3:42])[CH:15]=2)=[O:10])[CH2:2]1.C=O.[C:45]([BH3-])#N.[Na+]>CO.C(Cl)Cl>[CH3:45][N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][NH:8][C:9]([C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[C:20]([C:22](=[O:41])[NH:23][C:24]4[CH:29]=[C:28]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH:27]=[C:26]([NH:34][S:35]([CH3:38])(=[O:36])=[O:37])[C:25]=4[O:39][CH3:40])[CH:19]=[CH:18][C:17]=3[CH3:42])[CH:15]=2)=[O:10])[CH2:2]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 86592482HCID 86592482, compound

Product 1

HCID 10008897HCID 10008897, compoundYield 25.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. suspension of 106 mg (0.268 mmol) of 1-[5-(5-tert-Butyl-3-methanesulfonylamino-2-methoxy-phenylcarbamoyl)-2-methyl-phenyl]-1H-[1,2,3]triazole-4-carboxylic acid (piperidin-3-ylmethyl)-amide in 2 mL of MeOH containing 1% HOAc was added 70 μL of aqueous formaldehyde. The suspension was stirred at 0° C. for five minutes then 18 mg (0.281 mmol) of sodium cyanoborohydride was added and the mixture was warmed to rt. After stirring for ˜1 the reaction mixture was diluted with 40 mL of CH2Cl2 and washed with 25 mL of water. The aqueous wash was extracted with CH2Cl2 (2×25 mL), the combined organic extracts were dried (Na2SO4), filtered and evaporated to afford a yellow solid. Chromatography provided 42 mg of product. mp: 209–211. ESI MS (m/z 612, 100, M+H).

Workup

  1. temperaturethe mixture was warmed to rt
  2. stirringAfter stirring for ˜1 the reaction mixture
  3. washwashed with 25 mL of water
  4. washThe aqueous wash
  5. extractionwas extracted with CH2Cl2 (2×25 mL)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. customto afford a yellow solid

Sources & evidence

ORD record
ord-90953c9f0a4f45729473fd012b2bb96e
Source dataset
uspto-grants-2007_01
Patent number
US07166628B2

Reaction notes

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