Methylamine → HCID 90149152, compound

HRID 2202554Notes

Reaction equation

HRID 2202554 reaction equation
FC(F)(F)C([O-])=O.[CH2:8]([O:15][C:16]([NH:18][C@H:19]([C:28]1[NH:29][C:30]([C:33]2[CH:42]=[CH:41][C:40]3[C:35](=[CH:36][CH:37]=[C:38]([O:43][CH3:44])[CH:39]=3)[CH:34]=2)=[CH:31][NH+:32]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25](O)=[O:26])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:45][N:46](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CN>CN(C=O)C.CCOC(C)=O>[CH3:44][O:43][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[CH:34]=[C:33]([C:30]1[NH:29][C:28]([C@@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]([NH:46][CH3:45])=[O:26])=[N:32][CH:31]=1)[CH:42]=[CH:41]2

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 90120270HCID 90120270, compound

Product 1

HCID 90149152HCID 90149152, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of E2 in DMF (0.1 M) were added HATU (1.5 eq.) and DIPEA (2.0 eq.) followed after 10 min by methylamine (2.0 M solution in THF, 5 eq.). Reaction mixture was stirred at room temperature for 16 h, then it was diluted with EtOAc, washed with sat. aq. NaHCO3 sol., brine, dried over Na2SO4, filtered and concentrated to give a dark brown residue. The resulting crude was purified by column chromatography (eluent: petroleum ether/EtOAc from 9:1 to 100% EtOAc, then EtOAc/MeOH=95:5) to give the title compound as a colorless oil. MS (ES+) C30H34N4O4: 515 (M+H)+.

Workup

  1. customReaction mixture
  2. washwashed with sat. aq. NaHCO3 sol., brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a dark brown residue
  7. customThe resulting crude was purified by column chromatography (eluent

Sources & evidence

ORD record
ord-d89d634d42ee457bb1ddb8d1eda4d43a
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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