4-Methylmorpholine → HCID 68158302, compound

HRID 242915Notes

Reaction equation

HRID 242915 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:16]([O:20][C:21]([NH:23][C@@H:24]([CH3:28])[C:25](O)=[O:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:16]([O:20][C:21](=[O:22])[NH:23][C@H:24]([C:25](=[O:26])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][C:4]=1[NH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH3:28])([CH3:17])([CH3:18])[CH3:19]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 85082Tert-butoxycarbonylalanineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 584592164-Fluoro-N2-pyridin-3-ylbenzene-1,2-diamine

Product 1

HCID 68158302HCID 68158302, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-fluoro-N2-pyridin-3-ylbenzene-1,2-diamine (1.03 g, 5.07 mmol), (S)-2-tertbutoxycarbonylaminopropionic acid (1.05 g, 5.58 mmol), HOAt (759 mg, 5.58 mmol), 4-methylmorpholine (1.23 mL, 11.15 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (1.07 g, 5.58 mmol) in DCM (30 mL) was stirred at RT for 2 h. The reaction mixture was then partitioned between DCM and a saturated solution of NaHCO3. A precipitate was present in the organic fraction which was filtered off to afford the title compound as a pale yellow solid (503 mg). The filtrate was dried (MgSO4) and concentrated in vacuo and the resulting residue was triturated with DCM to afford a second batch of the title compound as a yellow solid (765 mg; 67% yield for the combined batches). LCMS (Method C): RT 2.06 min [M+H]+ 375.3

Workup

  1. customThe reaction mixture was then partitioned between DCM
  2. filtrationwas filtered off

Sources & evidence

ORD record
ord-2c1b62436b4a4e679e26ff3dd6e4b7e4
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…