Formaldehyde → HCID 178491360, compound

HRID 447925Notes

Reaction equation

HRID 447925 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH3:26])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][NH:17]2)[N:15]=1)=[NH:9].C=O.[C:29](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:26][O:25][C:21]1[CH:22]=[CH:23][CH:24]=[C:4]([O:3][CH3:2])[C:5]=1[CH2:6][NH:7][C:8]([NH:10][C:11]1[S:12][CH:13]=[C:14]([CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:29])[N:15]=1)=[NH:9]

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178491363HCID 178491363, compound

Product 1

HCID 178491360HCID 178491360, compoundYield 29.3%

Conditions

Temperature
10 °C

Procedure

To 72 mg (0.2 mmol) N-(2,6-dimethoxybenzyl)-N′-(4-pyrrolidine-2-yl-1,3-thiazole-2-yl)guanidine hydrochloride, Example 147, and 20 mg formaline (37% aqueous solution) were added 51 mg of sodium triacetoxyborohydride at 10° C., the mixture was then stirred for 30 minutes at 10° C. and 2 hours at room temperature. For workup, the mixture was evaporation-concentrated, the residue was dissolved in dichloromethane, was washed with water, was dried and was concentrated once again. Following chromatography of the crude product on RP-silica gel (Chromabond column, acetonitrile/water+0.1% glacial acetic acid; 0-100%), 22 mg of a white solid were obtained, ESI-MS [M+H+]=376.15.

Workup

  1. concentrationFor workup, the mixture was evaporation-concentrated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwas washed with water
  4. customwas dried
  5. concentrationwas concentrated once again

Sources & evidence

ORD record
ord-057462009c334f8aa46f15e50d356068
Source dataset
uspto-grants-2013_07
Patent number
US08481576B2

Reaction notes

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