Sarcosine → HCID 10229103, compound

HRID 131125Notes

Reaction equation

HRID 131125 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:15]([NH2:18])=[N:16][CH:17]=2)[CH:5]=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[NH:30]([CH2:32][C:33](O)=[O:34])[CH3:31].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:13]=[C:14]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=3[Cl:26])[C:15]([NH:18][C:33](=[O:34])[CH2:32][NH:30][CH3:31])=[N:16][CH:17]=2)[CH:5]=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 1088SarcosineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12086022HCID 12086022, compound

Product 1

HCID 10229103HCID 10229103, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of N5-{2-[(6-amino-5-nitropyridin-2-yl)amino]ethyl}-3-(2,4-dichlorophenyl)pyrazine-2,5-diamine (30 mg, 0.068 mmol) in THF (2 ml) were added sarcosine (26 mg, 0.138 mmol), HBTU (104.5 mg, 0.2756 mmol) and DIPEA (60 μl) and stirred overnight at 80° C. The mixture was cooled down to room temperature, concentrated and taken in ethyl acetate and water. The layers were separated and the organic layer was washed with water and brine, dried, concentrated and purified to afford the title product.

Workup

  1. temperatureThe mixture was cooled down to room temperature
  2. concentrationconcentrated
  3. customThe layers were separated
  4. washthe organic layer was washed with water and brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified

Sources & evidence

ORD record
ord-645105a1a3b1480aa8156c3223bda01c
Source dataset
uspto-grants-2008_06
Patent number
US07384942B2

Reaction notes

Loading…