Tert-butoxycarbonylalanine → HCID 68157069, compound

HRID 243158Notes

Reaction equation

HRID 243158 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.C1C=NC2N(O)N=NC=2C=1.[F:36][C:37]1[CH:38]=[C:39]([NH:44][C:45]2[CH:50]=[N:49][CH:48]=[CH:47][N:46]=2)[C:40]([NH2:43])=[CH:41][CH:42]=1>C(Cl)Cl.CN(C=O)C.O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([C:11](=[O:13])[NH:43][C:40]1[CH:41]=[CH:42][C:37]([F:36])=[CH:38][C:39]=1[NH:44][C:45]1[CH:50]=[N:49][CH:48]=[CH:47][N:46]=1)[CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 4

HCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68156972HCID 68156972, compound

Product 1

HCID 68157069HCID 68157069, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

N-(tert-Butoxycarbonyl)-L-alanine (150 mg, 0.78 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (165 mg, 0.86 mmol) and HOAt (106 mg, 0.78 mmol) were added to 4-fluoro-N2-pyrazin-2-yl-benzene-1,2-diamine (160 mg, 0.78 mmol) in DCM (10.0 ml) and DMF (1.00 ml) at 0° C. The reaction was stirred for 3 h then poured into water and the aqueous layer extracted with DCM (×3). The combined organic fractions were washed with brine, dried (Na2SO4) and concentrated in vacuo. The product was purified by chromatography (SiO2, 0-10% methanol/DCM) to yield the title compound (144 mg, 0.38 mmol, 50%). LCMS: RT 3.02 min [M+H]+ 376.2. 1H NMR (CDCl3, 400 MHz): δ 8.36 (1H, s), 8.12 (1H, dd, J2.8, 1.5 Hz), 8.03 (1H, br s), 8.02 (1H, d, J=2.7 Hz), 7.92 (1H, br s), 7.62 (1H, br s), 7.28 (1H, m), 6.77 (1H, td, J 8.4, 2.9 Hz), 4.97 (1H, br s), 4.20 (1H, m), 1.49 (3H, d, J 7.2 Hz), 1.45 (9H, s).

Workup

  1. extractionthe aqueous layer extracted with DCM (×3)
  2. washThe combined organic fractions were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by chromatography (SiO2, 0-10% methanol/DCM)

Sources & evidence

ORD record
ord-b95093a5466f4939bb5b9b6176fe1a8e
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…