Benzaldehyde → HCID 86705377, compound

HRID 707465Notes

Reaction equation

HRID 707465 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:12]3[S:13][C:14]4[CH2:19][NH:18][CH2:17][CH2:16][C:15]=4[C:11]=3[C:10]3=[N:20][CH:21]=[N:22][N:9]3[C:8]2=[O:23])=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:40](=O)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:12]3[S:13][C:14]4[CH2:19][N:18]([CH2:40][C:41]5[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=5)[CH2:17][CH2:16][C:15]=4[C:11]=3[C:10]3=[N:20][CH:21]=[N:22][N:9]3[C:8]2=[O:23])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86705378HCID 86705378, compound

Product 1

HCID 86705377HCID 86705377, compoundYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6-(4-Chlorobenzyl)-8,9,10,11-tetrahydropyrido[4′,3′:4,5]thieno[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (80 mg, 0.22 mmol), sodium tri(acetoxy)borohydride (68 mg, 0.32 mmol), benzaldehyde (27 mg, 0.25 mmol) and THF (2 ml) were combined and stirred at room temperature for 18 hours. The mixture was concentrated, diluted with methanol, filtered and purified via reverse phase HPLC to yield 102 (50 mg, 40%) as the trifluoroacetic acid salt.

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with methanol
  3. filtrationfiltered
  4. custompurified via reverse phase HPLC

Sources & evidence

ORD record
ord-e0ee1fadd7694ccdaee0ee1198dd7312
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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