Diisopropylethylamine → HCID 117856350, compound

HRID 509915Notes

Reaction equation

HRID 509915 reaction equation
[NH2:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1.FC(F)(F)C([O-])=O.[Br-].[NH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][N+:24]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])([CH2:28][CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=2)[CH2:23]1.NC1CCC[N+](CCCC2C=CC(OC)=CC=2)(CC(OCC)=O)C1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C)C=O>[Cl-:9].[NH2:1][C:2]1[C:3]([C:10]([NH:21][CH:22]2[CH2:27][CH2:26][CH2:25][N+:24]([CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41])([CH2:28][CH2:29][CH2:30][C:31]3[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=3)[CH2:23]2)=[O:12])=[N:4][C:5]([Cl:9])=[C:6]([NH2:8])[N:7]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 64521193,5-Diamino-6-chloro-pyrazine acid2×HCID 131733252HCID 131733252, compound2×

Product 1

HCID 117856350HCID 117856350, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-diamino-6-chloropyrazine-2-carboxylic-acid (Intermediate 1.1.1, 46 mg, 0.25 mmol), 3-amino-1-ethoxycarbonylmethyl-1-[3-(4-methoxy-phenyl)-propyl]-piperidinium bromide trifluoroacetate salt (Intermediate 3.1.2, 230 mg, 0.25 mmol), O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (86 mg, 0.27 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.1 mmol) in dry N,N-dimethylformamide (5 mL) is stirred for 5 hours at room temperature. The solution is concentrated under reduced pressure to half of the volume, water (2 mL) added and the mixture purified via preparative reverse phase HPLC (gradient of acetonitrile in water+0.05% trifluoroacetic acid). Fractions containing the title compound are concentrated under reduced pressure. The residue is treated with HCl in diethyl ether (2 M, 2 mL), the solvent removed and the residue dried at 50° C. under vacuum. Yield: 56 mg. IC50=0.15.

Workup

  1. concentrationThe solution is concentrated under reduced pressure to half of the volume, water (2 mL)
  2. additionadded
  3. customthe mixture purified via preparative reverse phase HPLC (gradient of acetonitrile in water+0.05% trifluoroacetic acid)
  4. additionFractions containing the title compound
  5. concentrationare concentrated under reduced pressure
  6. additionThe residue is treated with HCl in diethyl ether (2 M, 2 mL)
  7. customthe solvent removed
  8. customthe residue dried at 50° C. under vacuum

Sources & evidence

ORD record
ord-a3a5e5c9a2dd48328160d8f249c6d336
Source dataset
uspto-grants-2015_08
Patent number
US09096548B2

Reaction notes

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