Methylamine → HCID 68583722, compound

HRID 2235572Notes

Reaction equation

HRID 2235572 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:15][C:16]2[N:20]([CH3:21])[C:19]3[C:22]([N:26]([CH2:30][CH2:31][CH3:32])[CH2:27][CH2:28][CH3:29])=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][CH2:9][CH2:10][C:11](O)=[O:12].F[P-](F)(F)(F)(F)F.[N:40]1(OC(N(C)C)=[N+](C)C)[C:44]2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.CN>O1CCCC1.O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:15][C:16]2[N:20]([CH3:21])[C:19]3[C:22]([N:26]([CH2:27][CH2:28][CH3:29])[CH2:30][CH2:31][CH3:32])=[CH:23][CH:24]=[CH:25][C:18]=3[N:17]=2)=[C:6]([CH:14]=1)[O:7][CH2:8][CH2:9][CH2:10][C:11]([NH:40][CH3:44])=[O:12]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58896464HCID 58896464, compound

Product 1

HCID 68583722HCID 68583722, compoundYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of 20 mg (0.044 mmol) of 4-[5-chloro-2-[[7-(dipropylamino)-1-methyl-1H-benzimidazol-2-yl]amino]phenoxy]butyric acid in 2 mL of tetrahydrofuran was added 25 mg (0.065 mmol) of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU), 19 μL (0.11 mmol) of diisopropylethylamine, and 54 μL (0.11 mmol) of methylamine (2M solution in tetrahydrofuran). The reaction was stirred at room temperature for 3 h, diluted with water and extracted with dichloromethane. The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The thus obtained residue was purified via preparative TLC eluting with a 75% ethyl acetate/hexanes solution. The isolated product was washed off the silica with 100% ethyl acetate and concentrated in vacuo. The thus obtained residue was dissolved in methanol and hydrochloric acid (1N solution in diethyl ether) was added. The resulting slurry was concentrated in vacuo to give 9.0 mg (44%) of the title compound as the hydrochloric salt.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe thus obtained residue was purified via preparative TLC
  6. washeluting with a 75% ethyl acetate/hexanes solution
  7. washThe isolated product was washed off the silica with 100% ethyl acetate
  8. concentrationconcentrated in vacuo
  9. dissolutionThe thus obtained residue was dissolved in methanol
  10. additionhydrochloric acid (1N solution in diethyl ether) was added
  11. concentrationThe resulting slurry was concentrated in vacuo

Sources & evidence

ORD record
ord-b16377ace00e45c88be913efd4efab35
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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