Triphenylphosphine → HCID 178429386, compound

HRID 707393Notes

Reaction equation

HRID 707393 reaction equation
[OH:1][C@@H:2]1[CH2:5][C@H:4]([N:6]2[C:10]3=[N:11][CH:12]=[CH:13][N:14]=[C:9]3[C:8]([CH3:16])([CH3:15])[C:7]2=[O:17])[CH2:3]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[C:38]1[S:39][C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[S:39]1[C:40]2[CH:46]=[CH:45][CH:44]=[CH:43][C:41]=2[N:42]=[C:38]1[O:1][C@H:2]1[CH2:5][C@H:4]([N:6]2[C:10]3=[N:11][CH:12]=[CH:13][N:14]=[C:9]3[C:8]([CH3:15])([CH3:16])[C:7]2=[O:17])[CH2:3]1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178429385HCID 178429385, compoundHCID 178517143HCID 178517143, compound

Product 1

HCID 178429386HCID 178429386, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 5-(cis-3-hydroxycyclobutyl)-7,7-dimethyl-5H-pyrrolo[2,3-b]pyrazin-6(7H)-one (0.022 g, 0.094 mmol), triphenylphosphine (0.030 g, 0.113 mmol), 2-hydroxybenzothiazole (0.017 g, 0.113 mmol) in THF (2 mL) at 0° C. was added DIAD (0.028 mL, 0.141 mmol). The reaction mixture was stirred at room temperature overnight, concentrated, purified by reverse phase HPLC. The pure fractions were concentrated to minimal H2O, neutralized with saturated aqueous NaHCO3, and the off white solid was collected and dried (18.5 mg, 53.5%). MS (M+1):367.1. 1H NMR (400 MHz, MeOH) δ ppm 8.20 (1 H, d, J=3.1 Hz), 8.15 (1 H, d, J=3.1 Hz), 7.76 (1 H, dd, J=7.9, 0.7 Hz), 7.66 (1 H, d, J=7.6 Hz), 7.39 (1 H, td, J=7.8, 1.3 Hz), 7.19-7.34 (1 H, m), 5.79 (1 H, dt, J=7.0, 3.5 Hz), 5.25-5.42 (1 H, m), 3.40-3.56 (2 H, m), 2.68-2.86 (2 H, m), 1.38-1.50 (6 H, m). MS (M+1):367.1.

Workup

  1. concentrationconcentrated
  2. custompurified by reverse phase HPLC
  3. concentrationThe pure fractions were concentrated to minimal H2O
  4. customthe off white solid was collected
  5. customdried (18.5 mg, 53.5%)

Sources & evidence

ORD record
ord-75801e7139f942dc9b327cc5404e3b32
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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