Formaldehyde → HCID 11452964, compound

HRID 1837608Notes

Reaction equation

HRID 1837608 reaction equation
[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:27])[CH2:11][C:12]2[N:13]=[C:14]([NH:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)[S:15][CH:16]=2)=[N:6][CH:5]=1)([CH3:3])[CH3:2].C=O.O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl>[CH:1]([C:4]1[S:8][C:7]([NH:9][C:10](=[O:27])[CH2:11][C:12]2[N:13]=[C:14]([N:17]([CH3:31])[CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]3)[S:15][CH:16]=2)=[N:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 11246825HCID 11246825, compound

Product 1

HCID 11452964HCID 11452964, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-(5-isopropyl-1,3-thiazol-2-yl)-2-(2-{[2-(4-methyl-1piperazinyl)ethyl]amino}-1,3-thiazol-4-yl)acetamide (1 g, 2.45 mmol) and 40% formaldehyde in water (0.17 ml, 2.45 mmol) were mixed in CHCl3 (10 ml) and then treated with sodium triacetoxyborohydride (0.727 g, 3.43 mmol). The mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. The reaction mixture was quenched by adding aqueous saturated sodium bicarbonate and the product was extracted with CHCl3. The organic layer was washed with brine, dried and evaporated. The title compound was obtained after chromatographic purification in 75% yield.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding aqueous saturated sodium bicarbonate
  3. extractionthe product was extracted with CHCl3
  4. washThe organic layer was washed with brine
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-f3e9496f40004fd3a74e84e671e6f041
Source dataset
uspto-grants-2004_08
Patent number
US06784198B1

Reaction notes

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