Water → (1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine

HRID 1824269Notes

Reaction equation

HRID 1824269 reaction equation
[N:1]([C@@H:4]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C@H:5]1[NH:13][C:14]1[C:19]([CH:20]2[CH2:22][CH2:21]2)=[N:18][C:17]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])=[C:16]([CH:31]2[CH2:33][CH2:32]2)[N:15]=1)=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>C1COCC1>[CH:20]1([C:19]2[C:14]([NH:13][C@@H:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:12][C@H:4]3[NH2:1])=[N:15][C:16]([CH:31]3[CH2:32][CH2:33]3)=[C:17]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:18]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 58583346N-[(1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl]-3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-amine

Product 1

HCID 58583281(1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamineYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[(1R,2R)-2-azido-2,3-dihydro-1H-inden-1-yl]-3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-amine (0.55 g, 1.15 mmol) in anhydrous THF (30 mL) was added PPh3 (0.396 g, 1.51 mmol). The resulting mixture was stirred at rt for 3 hr. To the solution was added water (0.25 mL, 13.9 mmol). The reaction is then allowed to stir overnight at rt. The mixture is concentrated, and the resulting solid is dissolved in MeOH. Purify by passage over Biorad acidic resin by applying the MeOH solution onto the resin and rinsing the resin with MeOH. The resin was then rinsed with 5% triethylamine/MeOH solution to afford 0.52 g (75%) of (1R,2R)-N1-[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]-2,3-dihydro-1H-indene-1,2-diamine as a solid: 1H NMR (CDCl3) δ 0.85–1.12, 1.64–1.76, 1.89, 2.68–2.82, 3.31–3.39, 3.66–3.72, 5.16, 5.33, 7.28–7.53; MS (ESI+) for C25H24Cl2N4 m/z 451 (M+H)+.

Workup

  1. stirringto stir overnight at rt
  2. concentrationThe mixture is concentrated
  3. dissolutionthe resulting solid is dissolved in MeOH
  4. customPurify by passage over Biorad acidic resin
  5. washrinsing the resin with MeOH
  6. washThe resin was then rinsed with 5% triethylamine/MeOH solution

Sources & evidence

ORD record
ord-cf320dec2dce43b79a0f962622a158fb
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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