Dimethylamine → HCID 22346324, compound

HRID 897321Notes

Reaction equation

HRID 897321 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][NH:7][C:8]([C:10]2C(OC)=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[N:17]3)=[C:12]([NH:22][CH3:23])[N:11]=2)=[O:9])=[CH:4][CH:3]=1.[CH:26]([N:29]([CH:32](C)C)[CH2:30]C)(C)C.ClC(Cl)(O[C:39](=O)[O:40][C:41](Cl)(Cl)Cl)Cl.CNC.C1C[O:53]CC1>C(Cl)Cl>[CH3:26][N:29]([CH3:32])[C:30]([N:22]([CH3:23])[C:12]1[N:11]=[C:10]([C:8]([NH:7][CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:25][CH:24]=2)=[O:9])[C:39]([O:40][CH3:41])=[C:18]2[C:13]=1[CH:14]=[CH:15][CH:16]=[N:17]2)=[O:53]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 81531Diisopropylethylamine2×HCID 94429Triphosgene2×HCID 22346362HCID 22346362, compound

Product 1

HCID 22346324HCID 22346324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(4-fluorobenzyl)-8-methoxy-5-(methylamino)-1,6-naphthyridine-7-carboxamide(93 mg, 0.27 mmol) in CH2Cl2 (1 mL) at OC was added diisopropylethylamine (0.14 mL, 1.5 mmol) and triphosgene (0.04 g, 0.14 mmol) and the mixture was stirred at room temperature for 16 hr. Additional diisopropylethylamine (0.07 mL, 0.08 mmol) and triphosgene (0.02 g, 0.07 mmol) was added and the reaction was stirred an additional 16 hr at room temperature. A portion of this solution (0.5 mL) was treated with dimethylamine (0.41 mL of a 2M solution in THF, 0.82 mmol). The solvent was evaporated in vacuo and the residue dissolved in DMF (1 mL) and purified by reverse phase HPLC. (Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid which was used directly in step 3.

Workup

  1. stirringthe reaction was stirred an additional 16 hr at room temperature
  2. customThe solvent was evaporated in vacuo
  3. dissolutionthe residue dissolved in DMF (1 mL)
  4. custompurified by reverse phase HPLC
  5. wash(Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins)

Sources & evidence

ORD record
ord-9d95ff91090e4e6f95a3d2be85c6a5dc
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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