Methylamine → HCID 66672157, compound

HRID 1913491Notes

Reaction equation

HRID 1913491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[N:20]=[C:19]([N:21]([CH3:26])[CH2:22][C:23](O)=[O:24])[C:18]([C:27]#[N:28])=[C:17]([C:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][OH:38])=[CH:31][CH:30]=4)[C:16]=3[C:39]#[N:40])[N:12]=2)=[CH:4][CH:3]=1.[CH3:41][N:42](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[C:11]([CH2:13][S:14][C:15]3[N:20]=[C:19]([N:21]([CH3:26])[CH2:22][C:23]([NH:42][CH3:41])=[O:24])[C:18]([C:27]#[N:28])=[C:17]([C:29]4[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH2:37][OH:38])=[CH:33][CH:34]=4)[C:16]=3[C:39]#[N:40])[N:12]=2)=[CH:4][CH:3]=1

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 66671884HCID 66671884, compound

Product 1

HCID 66672157HCID 66672157, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

100 mg (0.162 mmol) of the compound from Example 34A were initially charged in 2 ml of DMF, cooled to 0° C., and 123 mg (0.324 mmol) of HATU were added. After 20 min, 243 μl (0.486 mmol) of methylamine and 56 ml (0.324 mmol) of N,N-diisopropylethylamine were added, and the mixture was then stirred at RT overnight. Water was added, and the reaction mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.15% conc. hydrochloric acid). This gave 37 mg of the desired compound. In addition, more solid precipitated from the aqueous phase overnight; this was filtered off and washed with a little water. This gave another 50 mg of the desired compound.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative HPLC (Chromasil, water/acetonitrile+0.15% conc. hydrochloric acid)
  6. customIn addition, more solid precipitated from the aqueous phase overnight
  7. filtrationthis was filtered off
  8. washwashed with a little water

Sources & evidence

ORD record
ord-3e7532cd04d3469f90f0e3e4753dad58
Source dataset
uspto-grants-2013_12
Patent number
US08609686B2

Reaction notes

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