Dichloromethane → HCID 90449300, compound

HRID 925507Notes

Reaction equation

HRID 925507 reaction equation
ClC1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][NH:13][CH3:14])=[C:5]2[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH3:26])([CH3:25])[C:23]#[N:24])=[CH:18][CH:17]=1.ClC(Cl)(O[C:31](=[O:37])OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.Cl[CH2:47][Cl:48]>>[Cl:48][C:47]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[CH2:12][N:13]([CH3:14])[C:31](=[O:37])[N:15]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:26])[C:23]#[N:24])=[CH:18][CH:17]=4)[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 94429TriphosgeneHCID 89589821HCID 89589821, compound

Product 1

HCID 90449300HCID 90449300, compound

Procedure

2-(4-((6-chloro-3-((methylamino)methyl)-1,5-naphthyridin-4-yl)amino)phenyl)-2-methylpropionitrile (2.0 g, 5.5 mmol) was dissolved in dichloromethane (25 mL), to the reaction flask in an ice bath added triphosgene (1.8 g, 6.1 mmol) and triethylamine (0.7 mL). Then, the mixture was stirred at room temperature for 2 h. The reaction was quenched with a saturated aqueous solution of sodium carbonate, extracted with 100 mL of dichloromethane, the organic layer was dried over anhydrous sodium sulfate, the solvent was removed under reduced pressure to give 1.6 g of a pale yellow solid.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of sodium carbonate
  2. extractionextracted with 100 mL of dichloromethane
  3. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-48cf703e912f47f4be6d9e8b6bf600ab
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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