1,3,5-Trioxane → HCID 54762221, compound

HRID 1467331Notes

Reaction equation

HRID 1467331 reaction equation
[C:1]1([CH:7]2[CH2:12][NH:11][CH2:10][CH:9]([NH:13][C:14]([C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[NH:21][N:20]=[C:19]4[C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[O:15])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1COCO[CH2:32]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C.ClCCl>[CH3:32][N:11]1[CH2:12][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH:9]([NH:13][C:14]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[NH:21][N:20]=[C:19]3[C:25]2[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=2)=[O:15])[CH2:10]1

Participants

6

Reactant 3

HCID 80811,3,5-TrioxaneHCID 5049666Sodium triacetoxyborohydrideHCID 56591357HCID 56591357, compound

Product 1

HCID 54762221HCID 54762221, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

In a flask, dichloromethane (1 mL) and acetic acid (1 drop) was added to N-(5-phenylpiperidin-3-yl)-3-(pyridin-4-yl)-1H-indazole-5-carboxamide (0.05 mmol) and 1,3,5-trioxane (0.2 mmol). The reaction was stirred for 60 minutes. Sodium triacetoxyborohydride (1 mmol) was added in one portion. The reaction was stirred for 1 h. The reaction was concentrated in vacuo and purified using prep LC/MS.

Workup

  1. stirringThe reaction was stirred for 1 h
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified

Sources & evidence

ORD record
ord-1f45410bbae14c578d078f6004d7364a
Source dataset
uspto-grants-2015_04
Patent number
US08999957B2

Reaction notes

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