Hydrochloric Acid → N-(5-cyanopyrazin-2-yl)-7-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

HRID 1778075Notes

Reaction equation

HRID 1778075 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22](OC)[O:23]C)[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].Cl>>[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([CH:22]=[O:23])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 118036535N-(5-cyanopyrazin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide2×

Product 1

HCID 118037084N-(5-cyanopyrazin-2-yl)-7-formyl-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide

Procedure

N-(5-cyanopyrazin-2-yl)-7-(dimethoxymethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 2A, 32 mg, 0.090 mmol) was treated with HCl (4M in dioxane, 2 ml, 65.8 mmol) and stirred at room temperature for 1 h. The reaction mixture was concentrated under vacuum to dryness. The crude material was purified by normal phase chromatography (4 g silica gel cartridge, DCM/(DCM/MeOH 9:1) 100:0 to 0:100). The product containing fraction was collected and concentrated under vacuum to obtain the title compound as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum to dryness
  2. customThe crude material was purified by normal phase chromatography (4 g silica gel cartridge, DCM/(DCM/MeOH 9:1) 100:0 to 0:100)
  3. additionThe product containing fraction
  4. customwas collected
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fb01f7a5d3a8496cb1f4e85237a7a565
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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