4-Methylmorpholine → HCID 118308304, compound

HRID 1750695Notes

Reaction equation

HRID 1750695 reaction equation
Cl.[F:2][C:3]([F:18])([F:17])[C:4]1[N:5]=[CH:6][C:7]([NH:10][C@H:11]2[CH2:15][CH2:14][CH2:13][C@@H:12]2[NH2:16])=[N:8][CH:9]=1.[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=1[C:22](O)=[O:23].[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.CN1CCOCC1>CN(C=O)C.CO>[F:19][C:20]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[C:21]=1[C:22]([NH:16][C@H:12]1[CH2:13][CH2:14][CH2:15][C@@H:11]1[NH:10][C:7]1[CH:6]=[N:5][C:4]([C:3]([F:2])([F:17])[F:18])=[CH:9][N:8]=1)=[O:23]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27373602-Fluoro-6-methoxybenzoic acidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×

Product 1

HCID 118308304HCID 118308304, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 14 mg, 0.05 mmol), 2-fluoro-6-methoxybenzoic acid (CAS number 137654-21-8; 8.5 mg, 0.05 mmol), TOTU (20 mg, 0.06 mmol) and 4-methylmorpholine (0.008 ml, 0.075 mmol) in DMF (0.25 ml) was stirred at room temperature for 1 hour. The reaction was then diluted with methanol and concentrated in vacuo. The resulting residue was purified by reverse phase preparative HPLC (eluted with acetonitrile/water with 0.1% ammonia) to afford the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resulting residue was purified by reverse phase preparative HPLC (eluted with acetonitrile/water with 0.1% ammonia)

Sources & evidence

ORD record
ord-5d4f70109ecf4e5ba78031d82fc4c3d9
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

Loading…