Formaldehyde → HCID 9978016, compound

HRID 2118034Notes

Reaction equation

HRID 2118034 reaction equation
C=O.[Cl:3][C:4]1[CH:29]=[CH:28][C:7]2[N:8]3[C:12]([CH2:13][NH:14][CH2:15][C:6]=2[CH:5]=1)=[N:11][N:10]=[C:9]3[CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:18][CH2:17]1.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:3][C:4]1[CH:29]=[CH:28][C:7]2[N:8]3[C:12]([CH2:13][N:14]([CH3:30])[CH2:15][C:6]=2[CH:5]=1)=[N:11][N:10]=[C:9]3[CH:16]1[CH2:21][CH2:20][N:19]([C:22]2[N:23]=[CH:24][CH:25]=[CH:26][N:27]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21925629HCID 21925629, compound

Product 1

HCID 9978016HCID 9978016, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Formaldehyde (37% w/v aqueous, 0.1 ml, 1.2 mmol) was added to a solution of the amine of example 12 (100 mg, 0.26 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 0.25 hours before sodium triacetoxyborohydride (111 mg, 0.53 mmol) was added, and the reaction mixture was stirred for a further 18 hours. The mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml). The organic layer was evaporated under reduced pressure and purified by chromatography on silica gel using methanol in dichloromethane (5:95) as eluant to afford the title compound as a brown foam (66 mg).

Workup

  1. additionwas added
  2. customThe mixture was partitioned between 2N aqueous sodium hydroxide solution (10 ml) and dichloromethane (10 ml)
  3. customThe organic layer was evaporated under reduced pressure
  4. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-508d636d65f644208a6ce29d0ce9cbc1
Source dataset
uspto-grants-2008_10
Patent number
US07442795B2

Reaction notes

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