Dimethylamine → HCID 12150098, compound

HRID 1884604Notes

Reaction equation

HRID 1884604 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:37][S:38]([CH3:41])(=[O:40])=[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:31](O)=[O:32])[CH:26]=3)=[CH:16][CH:15]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:43][N:44](C)[CH2:45]CCN=C=NCC.C(N(CC)CC)C.CNC>CN(C=O)C.O>[CH3:43][N:44]([CH3:45])[C:31]([C:27]1[CH:26]=[C:25]([O:24][C:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14]([NH:13][C:12]([NH:11][C:9]3[CH:10]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[CH:6]=[C:7]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[C:8]=3[O:35][CH3:36])=[O:34])=[CH:15][CH:16]=2)[CH:30]=[CH:29][N:28]=1)=[O:32]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12150097HCID 12150097, compound

Product 1

HCID 12150098HCID 12150098, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution (0° C.) of 4-{4-[3-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-ureido]-naphthalen-1-yloxy}-pyridine-2-carboxylic acid (Example 12) (58 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, 93:7) to give the title compound as a light tan solid (42 mg, 70% 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, 93:7)

Sources & evidence

ORD record
ord-c5097316253844808f5940261e6e4376
Source dataset
uspto-grants-2004_07
Patent number
US06765009B2

Reaction notes

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