Diethylamine → HCID 135519383, compound

HRID 1726110Notes

Reaction equation

HRID 1726110 reaction equation
C(NP(CC1C=C2C(=CC=1)NN=C2C1NC2C(C=1)=CC=CC=2)(C1C=CC=CC=1)=O)C.[N+](C1C=CC([O:40][P:41]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)(=[O:61])[O:42][C:43]2[CH:44]=[C:45]3[C:49](=[CH:50][CH:51]=2)[NH:48][N:47]=[C:46]3[C:52]2[NH:53][C:54]3[C:59]([CH:60]=2)=[CH:58][CH:57]=[CH:56][CH:55]=3)=CC=1)([O-])=O.C(NCC)C.N12CCCN=C1CCCCC2>ClCCl>[NH:53]1[C:54]2[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=2)[CH:60]=[C:52]1[C:46]1[C:45]2[C:49](=[CH:50][CH:51]=[C:43]([O:42][P:41]([C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)(=[O:40])[OH:61])[CH:44]=2)[NH:48][N:47]=1

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136342066HCID 136342066, compoundHCID 136342069HCID 136342069, compound

Product 1

HCID 135519383HCID 135519383, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

For the purpose of preparing the compound [3-(1H-indol-2-yl)-1H-indazol-5-ylmethyl]phenylphosphinic acid N-ethylamide, a solution of 150 mg of phenyl-phosphonic acid 3-(1H-indol-2-yl)-1H-indazol-5-yl ester 4-nitrophenyl ester (prepared according to procedure E) and 1.5 ml of diethylamine (2M solution in tetrahydrofuran) in dichloromethane (stabilized with amylene) is stirred at ambient temperature. 44 μl of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) are added and the medium is stirred overnight at ambient temperature. The solvent is evaporated off in a rotary evaporator and the reaction crude is purified by preparative LC/MS so as to isolate a compound of mass [M+H]+=390, which does not correspond to the expected product. A second fraction of 23 mg of a gray solid identified as phenylphosphonic acid mono-[3-(1H-indol-2-yl)-1H-indazol-5-yl]ester are collected.

Workup

  1. customThe solvent is evaporated off in a rotary evaporator
  2. customthe reaction crude
  3. customis purified by preparative LC/MS so as
  4. customto isolate a compound of mass [M+H]+=390, which

Sources & evidence

ORD record
ord-9c55a6423ac243f9b381dbcaa79dd4df
Source dataset
uspto-grants-2009_02
Patent number
US07491710B2

Reaction notes

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