Acetic Acid → HCID 44477250, compound

HRID 2361674Notes

Reaction equation

HRID 2361674 reaction equation
[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:17][CH:16]([NH:18][C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:15]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[BH3-][C:30]#N.[Na+].C(O)(=O)C>CC#N.O.C=O>[CH:1]1([N:5]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([N:14]3[CH2:15][CH:16]([N:18]([CH3:30])[C:19]4[CH:20]=[CH:21][C:22]([C:25]([NH:27][CH3:28])=[O:26])=[N:23][CH:24]=4)[CH2:17]3)=[O:13])[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 44477249HCID 44477249, compound

Product 1

HCID 44477250HCID 44477250, compoundYield 19%

Reagents, catalysts & solvents 2

HCID 712FormaldehydeSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

5-({1-[(4-cyclobutyl-1,4-diazepan-1-yl)carbonyl]azetidin-3-yl}amino)-N-methylpyridine-2-carboxamide (34 mg, 92 μmol) was dissolved in 1:1 MeCN/water (3 ml) and formaldehyde (50 μl of a 37% wt. soln, 1.8 mmol) followed by NaBH3CN (34 mg, 0.56 mmol) were added. After 10 minutes, acetic acid (40 μl, 0.72 mmol) was added and the reaction stirred at room temperature for 16 hours. The reaction mixture was concentrated at reduced pressure and purified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 90:10:1) giving the title compound as colourless oil (7 mg, 19%).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated at reduced pressure
  3. custompurified by FCC (DCM/MeOH/NH3 gradient, 98:2:1 to 90:10:1)

Sources & evidence

ORD record
ord-400c61a7d2b14ebe990964b0e7d4f4b0
Source dataset
uspto-grants-2014_04
Patent number
US08691804B2

Reaction notes

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