Acetic Acid → HCID 72706323, compound

HRID 707482Notes

Reaction equation

HRID 707482 reaction equation
[C:1]([C:4]1[CH:13]=[N:12][C:11]2[N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=3)[C:9](=[O:23])[N:8]3[N:24]=[CH:25][N:26]=[C:7]3[C:6]=2[CH:5]=1)(=O)[CH3:2].[CH3:27][C@@H:28]1[O:33][C@H:32]([CH3:34])[CH2:31][NH:30][CH2:29]1.C(O)(=O)C.C([BH3-])#N.[Na+]>C(#N)C>[CH3:27][C@H:28]1[CH2:29][N:30]([CH:1]([C:4]2[CH:13]=[N:12][C:11]3[N:10]([CH2:14][C:15]4[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=4)[C:9](=[O:23])[N:8]4[N:24]=[CH:25][N:26]=[C:7]4[C:6]=3[CH:5]=2)[CH3:2])[CH2:31][C@@H:32]([CH3:34])[O:33]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6415002,6-Dimethylmorpholine, cis-HCID 5003444Sodium cyanoborohydrideHCID 86705394HCID 86705394, compound

Product 1

HCID 72706323HCID 72706323, compoundYield 30.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

9-Acetyl-6-(4-methoxybenzyl)pyrido[3,2-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one (67 mg, 0.19 mmol), (2S,6R)-2,6-dimethylmorpholine (0.060 ml, 0.49 mmol), acetonitrile (1 ml) and acetic acid (0.020 mL, 0.35 mmol) were combined and stirred for 10 minutes. Sodium cyanoborohydride (18 mg, 0.29 mmol) was added and the mixture was stirred for 3 days at 50° C. The mixture was filtered and purified by preparative HPLC to afford 26 mg (23%) of 266 as a white solid.

Workup

  1. stirringthe mixture was stirred for 3 days at 50° C
  2. filtrationThe mixture was filtered
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8dcb69059bc34456a82be88415b2ebbd
Source dataset
uspto-grants-2015_11
Patent number
US09175010B2

Reaction notes

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