Methylamine → HCID 25256396, compound

HRID 1695551Notes

Reaction equation

HRID 1695551 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C@@:9]1([C:44](SCC#N)=[O:45])[C@:40]2([CH3:41])[C@H:12]([C@H:13]3[C@H:37]([C@@H:38]([OH:42])[CH2:39]2)[C@@:17]2([CH3:43])[CH2:18][C:19]4[CH:20]=[N:21][N:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH2:32][O:33][CH2:34][CH:35]=[CH2:36])[CH:26]=5)[C:23]=4[CH:24]=[C:16]2[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:7].[CH3:50][NH2:51]>C(#N)C.C(O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8][C@@:9]1([C:44](=[O:45])[NH:51][CH3:50])[C@:40]2([CH3:41])[C@H:12]([C@H:13]3[C@H:37]([C@@H:38]([OH:42])[CH2:39]2)[C@@:17]2([CH3:43])[CH2:18][C:19]4[CH:20]=[N:21][N:22]([C:25]5[CH:30]=[CH:29][C:28]([F:31])=[C:27]([CH2:32][O:33][CH2:34][CH:35]=[CH2:36])[CH:26]=5)[C:23]=4[CH:24]=[C:16]2[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)=[O:7]

Participants

5

Reactant 2

HCID 6329MethylamineHCID 25256298HCID 25256298, compound

Product 1

HCID 25256396HCID 25256396, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

In a 100 mL round-bottomed flask was dissolved the product obtained in Example 77 (75 mg, 0.11 mmol) in acetonitrile (2.5 mL) to give a yellow solution. 33% methanamine (2.5 mL, 20.19 mmol) in ethanol was added. The mixture was stirred in a closed flask for 3 hours, monitoring the reaction by LC-MS. When almost all of the starting material had been consumed, the volatiles were removed in vacuo. The crude mixture was purified on preparative HPLC (acetonitrile/water), and 15 mg (25%) was obtained of the desired product as a white solid after freeze-drying the pure fractions.

Workup

  1. customto give a yellow solution
  2. customthe reaction by LC-MS
  3. customWhen almost all of the starting material had been consumed
  4. customthe volatiles were removed in vacuo
  5. customThe crude mixture was purified on preparative HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-2296fe48441b411f9e3218def96361d4
Source dataset
uspto-grants-2012_04
Patent number
US08163724B2

Reaction notes

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