P,P-Diphenylphosphinic azide → HCID 46200788, compound

HRID 1966461Notes

Reaction equation

HRID 1966461 reaction equation
[CH2:1]([NH:8][C:9]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)[CH:15]=[CH:14]C=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([OH:34])[CH3:33].N.C1(P([N:50]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>C1COCC1>[CH2:1]([NH:8][C:9]1[CH:17]=[C:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24](=[O:31])[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:19]2)[CH:15]=[CH:14][C:33]=1[C:32]([NH2:50])=[O:34])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 199401P,P-Diphenylphosphinic azideHCID 22020343Ethanol, reaction products with ammonia, distn. residuesHCID 584256602-(Benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid

Product 1

HCID 46200788HCID 46200788, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(benzylamino)-4-(4-benzoylpiperazin-1-yl)benzoic acid (80 mg, 0.2 mmol), 2 M ammonia ethanol solution (0.60 ml, 1.2 mmol), tiethylamine (0.08 ml, 0.57 mmol) and diphenylphosphoryl azide (0.045 ml, 0.2 mmol) in 15 ml THF was stirred for 16 hours. The run was quenched with 1 ml water and all the solvents were evaporated under vacuum. 2-(benzylamino)-4-(4-bezoylpiperazin-1-yl)benzamide (40 mg, 40%) was obtained by flash column chromatograph (60% ethyl acetate in hexanes), and its hydrochloride was made by bubbling HCL gas in ether solution. 1H NMR (500 MHz, DMSO-d6) δ (ppm) 3.28-3.670 (br, 8H), 4.43 (s, 2H), 5.00 (s, 1H), 6.06 (s, 1H), 6.24 (d, J=8.2 Hz, 1H), 7.00 (s, 1H), 7.12-7.65 (m, 13H), 7.67 (d, J=8.8 Hz, 1H). 13C NMR (125 MHz, DMSO-d6): δ (ppm) 43.5, 46.0, 95.3, 102.7, 127.0, 127.3, 128.3, 128.4, 128.5, 128.6, 129.6, 132.4, 136.0, 139.3, 151.7, 154.2, 167.0, 168.9.

Workup

  1. customThe run was quenched with 1 ml water and all the solvents
  2. customwere evaporated under vacuum

Sources & evidence

ORD record
ord-9503ecd5c6b44a3eb6ce9a3e4225965e
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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