Methylamine → (S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate

HRID 2202561Notes

Reaction equation

HRID 2202561 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:21]1[O:22][C:23]([C:26]2[C:27]([O:36][CH3:37])=[N:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:24][N:25]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](O)=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:38][N:39](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>[CH3:37][O:36][C:27]1[C:26]([C:23]2[O:22][C:21]([C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH:39][CH3:38])=[O:19])=[N:25][CH:24]=2)=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28]=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 90149568(S)-7-(((benzyloxy)carbonyl)amino)-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)heptanoic acid

Product 1

HCID 90149176(S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of F5 in DMF (0.1 M) were added HATU (2.0 eq.) and DIPEA (3.0 eq.) followed after 10 min by methylamine (2.0 M solution in THF, 5.0 eq.). Reaction mixture was stirred at room temperature for 16 h. Then, reaction mixture was diluted with EtOAc, washed with sat. aq. NaHCO3, brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting crude was purified by column chromatography (eluent: Petroleum ether/EtOAc from 1:1 to 100% EtOAc, then EtOAc/MeOH=95:5) to give the title compound as pale yellow solid. MS (ES+) C29H32N4O5: 517 (M+H)+.

Workup

  1. customReaction mixture
  2. customThen, reaction mixture
  3. washwashed with sat. aq. NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude was purified by column chromatography (eluent

Sources & evidence

ORD record
ord-e38efdc0bf05487090e6c2cee57928b7
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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