3-Aminopropionitrile → HCID 178425214, compound

HRID 1500993Notes

Reaction equation

HRID 1500993 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][N:20](C)CCCN=C=NCC.[OH:30][C:31]1[C:39]2N=N[NH:36][C:35]=2[CH:34]=[CH:33][CH:32]=1.[CH2:40](N(CC)CC)C.NCCC#N>ClCCl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:20][CH2:19][C:32]2[C:31]([OH:30])=[N:36][C:35]([CH3:39])=[CH:34][C:33]=2[CH3:40])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 16473-AminopropionitrileHCID 8471TriethylamineHCID 738804-(Benzyloxy)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300, compound

Product 1

HCID 178425214HCID 178425214, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzyloxy)benzoic acid (228 mg, 1 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (210 mg, 1.1 mmol) and hydroxybenzotriazole (149 mg, 1.1 mmol) in dichloromethane (30 mL) was added triethylamine (202 mg, 2 mmol). The reaction mixture was stirred at room temperature for 1 hour, then 3-aminopropanenitrile (156 mg, 1 mmol) was added. The reaction mixture was stirred at room temperature overnight. After the reaction, the mixture was washed with saturated solution of sodium bicarbonate (10 mL×3), dried over anhydrous sodium sulfate to give crude product which was purified by column chromatography (silica gel, dichloromethane/methanol=50:1) to give 4-(benzyloxy)-N-((2-hydroxy-4,6-dimethylpyridin-3-yl)methyl)benzamide (Compound I-12) (110 mg, 30%). LRMS (M+H+) m/z: calcd 451.11. found 451. 1H NMR (300 MHz, d6-DMSO) δ11.47 (s, 1H), 8.20 (s, 1H), 7.82 (d, J=8.7 Hz, 2H), 7.49-7.35 (m, 5H), 7.05 (d, J=8.7 Hz, 2H), 5.88 (s, 1H), 5.17 (s, 1H), 4.30 (d, J=4.8 Hz, 2H), 2.19 (s, 1H), 2.13 (s, 1H).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customAfter the reaction
  3. washthe mixture was washed with saturated solution of sodium bicarbonate (10 mL×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto give crude product which
  6. customwas purified by column chromatography (silica gel, dichloromethane/methanol=50:1)

Sources & evidence

ORD record
ord-c577feb01a4a4651ac7f82c042d9250f
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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