Dimethylformamide → HCID 67496481, compound

HRID 1628234Notes

Reaction equation

HRID 1628234 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.CN(C(ON1N=N[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:35]([O:39][C:40]([C@@H](CC1C=CC=CC=1)C(O)=O)=[O:41])([CH3:38])([CH3:37])[CH3:36].CC[N:55](C(C)C)[CH:56]([CH3:58])[CH3:57].CN(C=[O:66])C>>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:57](=[O:66])[C@@H:56]([NH:55][C:40](=[O:41])[O:39][C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:58][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 447548695-Bromo-2-methoxypyridin-3-amineHCID 67089511HCID 67089511, compound

Product 1

HCID 67496481HCID 67496481, compoundYield 70%

Conditions

Temperature
50 °C

Procedure

To a 100 ml flask was added 5-bromo-2-methoxypyridin-3-amine 15.1.A (15 g, 74 mmole, available from Asymchem), HBTU (42 g, 111 mmoles), (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (24 g, 89 mmole) of, 150 ml of DMF and 26 mL of DIEA. The reaction was stirred at 50° C. for 24 hours, at which time the reaction was quenched with water (500 ml) and extracted with EtAc (1000 ml). The organic layer was extracted three more times with water (200 mL) and the solvent was removed by rotary evaporation. The crude product was recrystallized in MeOH/H2O (3/1) to give (S)-tert-butyl 1-(5-bromo-2-methoxypyridin-3-ylamino)-1-oxo-3-phenylpropan-2-ylcarbamate 15.1.B as white crystals (23.4 g, 70% yield).

Workup

  1. customwas quenched with water (500 ml)
  2. extractionextracted with EtAc (1000 ml)
  3. extractionThe organic layer was extracted three more times with water (200 mL)
  4. customthe solvent was removed by rotary evaporation
  5. customThe crude product was recrystallized in MeOH/H2O (3/1)

Sources & evidence

ORD record
ord-98c455ab33aa41dcb405b098800b249a
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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