Dimethylamine → HCID 10121131, compound

HRID 1884606Notes

Reaction equation

HRID 1884606 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:37][C:38]([O:40][CH3:41])=[O:39])[C:8]([O:35][CH3:36])=[C:9]([NH:11][C:12](=[O:34])[NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27](C(O)=O)[CH:26]=3)=[CH:16][CH:15]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C.CNC.[CH3:64][N:65]([CH:67]=[O:68])[CH3:66]>O>[CH3:41][O:40][C:38](=[O:39])[NH:37][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[C:9]([NH:11][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][C:25]3[CH:30]=[CH:29][N:28]=[C:27]([C:67](=[O:68])[N:65]([CH3:66])[CH3:64])[CH:26]=3)=[CH:16][CH:15]=2)=[O:34])[C:8]=1[O:35][CH3:36]

Participants

7

Reactant 5

HCID 674DimethylamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12150102HCID 12150102, compound

Product 1

HCID 10121131HCID 10121131, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution (0° C.) of 4-{4-[3-(5-tert-butyl-2-methoxy-3-methoxycarbonylamino-phenyl)-ureido]-naphthalen-1-yloxy}-pyridine-2-carboxylic acid (Example 14) (56 mg, 0.1 mmol) in DMF (1 mL) was added 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (23 mg, 0.12 mmol) and triethyl amine (0.070 mL, 0.5 mmol). The solution was allowed to stir at 0° C. for 30 min, then dimethylamine (2M solution in THF, 0.25 mL, 0.5 mmol) was added in one portion. The resulting solution was allowed to stir at room temperature for 12 h. Water (4 mL) was added and the product was extracted with EtOAc, dried over magnesium sulfate and concentrated via rotary evaporation. The resulting crude solid was purified by column chromatography (CH2Cl2:MeOH, 95:5) to provide the title compound as a light tan solid (45 mg, 77% yield).

Workup

  1. stirringto stir at room temperature for 12 h
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated via rotary evaporation
  5. customThe resulting crude solid was purified by column chromatography (CH2Cl2:MeOH, 95:5)

Sources & evidence

ORD record
ord-ad4a16f67dc546ebb09dcc826d6597a7
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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