Formaldehyde → (3-Ethynyl-pyrrolidin-1-yl)-[1-(7-methyl-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohept[f]inden-10-yl)-azetidin-3-yl]-methanone

HRID 528779Notes

Reaction equation

HRID 528779 reaction equation
[C:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:13][N:12]([C:14]3[N:15]4[C:19]([N:20]=[C:21]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23][C:22]=35)=[CH:18][CH:17]=[N:16]4)[CH2:11]2)=[O:9])[CH2:4]1)#[CH:2].C=O.[C:30](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.O>[C:1]([CH:3]1[CH2:7][CH2:6][N:5]([C:8]([CH:10]2[CH2:11][N:12]([C:14]3[N:15]4[C:19]([N:20]=[C:21]5[CH2:27][CH2:26][N:25]([CH3:30])[CH2:24][CH2:23][C:22]=35)=[CH:18][CH:17]=[N:16]4)[CH2:13]2)=[O:9])[CH2:4]1)#[CH:2]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86667178(3-Ethynyl-pyrrolidin-1-yl)-[1-(6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidin-3-yl]-methanone

Product 1

HCID 86667179(3-Ethynyl-pyrrolidin-1-yl)-[1-(7-methyl-6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohept[f]inden-10-yl)-azetidin-3-yl]-methanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 50 mg (0.14 mmol) of (3-Ethynyl-pyrrolidin-1-yl)-[1-(6,7,8,9-tetrahydro-5H-1,4,7,10a-tetraaza-cyclohepta[f]inden-10-yl)-azetidin-3-yl]-methanone in 2 mL of THF and 1 mL of puffer solution (pH 5) was added 11.3 μL (0.15 mmol) of formaldehyde (37% in water) and 35 mg (0.17 mmol) of sodium triacetoxyborohydride. Stirring was continued overnight, the reaction mixture diluted with 1 mL of water, filtered and purified by HPLC.

Workup

  1. filtrationfiltered
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-7c992917dcdd4a39b29cce8e560f387a
Source dataset
uspto-grants-2016_05
Patent number
US09346816B2

Reaction notes

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