Triphenylphosphine → HCID 68949948, compound

HRID 1453873Notes

Reaction equation

HRID 1453873 reaction equation
[CH3:1][N:2]([CH2:22][CH:23](O)[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C:3]([C:5]1[NH:9][N:8]=[C:7]([C:10]([O:12][CH3:13])=[O:11])[C:6]=1[O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:15]([O:14][C:6]1[C:7]([C:10]([O:12][CH3:13])=[O:11])=[N:8][N:9]2[CH:23]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)[CH2:22][N:2]([CH3:1])[C:3](=[O:4])[C:5]=12)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178499185HCID 178499185, compound

Product 1

HCID 68949948HCID 68949948, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-N-[2-hydroxy-2-(pyridin-3-yl)ethyl]-4-benzyloxy-3-methoxycarbonyl-1H-pyrazole-5-carboxamide (1.0 g, 2.44 mmol) and triphenylphosphine (2.24 g, 8.53 mmol) in THF (30 mL) was added diethyl azodicarboxylate (1.55 mL, 8.53 mmol) dropwise over a period of 5 minutes. The mixture was stirred for 2 hours. The solvent was removed in vacuo and the residue was purified by preparative HPLC (Waters prep LC 4000 System using a Waters Nova Pak column (3 100×40 mm I.D. cartridges, C18, 6 μM pore size) eluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) at 60 mL/minute). Appropriate fractions were combined and the solvents were removed under reduced pressure to give a gum. 1H NMR (400 MHz, d6-DMSO) δ 8.66 (s, 1H), 8.50 (s, 1H), 7.5-7.6 (m, 4H), 7.3-7.4 (m, 3H), 5.96 (t, J=4.4 Hz, 1H), 5.28 (AB quartet, J=10.9 Hz, 2H), 4.20 (dd, J=13, 4.2 Hz, 1H), 4.00 (dd, J=13, 4.4 Hz, 1H), 3.76 (s, 3H), 2.97 (s, 3H); ES MS (M+1)=393.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by preparative HPLC (Waters prep LC 4000 System
  3. washeluting with 95-5% water (0.10% TFA)/acetonitrile (0.10% TFA) at 60 mL/minute)
  4. customthe solvents were removed under reduced pressure
  5. customto give a gum

Sources & evidence

ORD record
ord-70cf120bd1c647beb8322e405d198a6d
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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