Diisopropylethylamine → HCID 44219448, compound

HRID 1949326Notes

Reaction equation

HRID 1949326 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=3)[N:11]=[C:10]([C:21]([OH:23])=O)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.ClC1C=C(N2C(C3C=CC=C(OCCO)C=3)=CC(C([N:57]3[CH2:61][C:60](=[O:62])[NH:59][CH2:58]3)=O)=N2)C=CC=1>C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]([C:13]3[CH:14]=[C:15]([C:19]#[N:20])[CH:16]=[CH:17][CH:18]=3)[N:11]=[C:10]([C:21]([N:57]3[CH2:61][C:60](=[O:62])[NH:59][CH2:58]3)=[O:23])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58277320HCID 58277320, compoundHCID 58277360HCID 58277360, compound

Product 1

HCID 44219448HCID 44219448, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The preparation of the title compound takes place starting from the compound of Example 110A using 3.2 equivalents of N,N-diisopropylethylamine and with the addition of 0.1% formic acid in the preparative HPLC in analogy to the synthesis of the compound of Example 23. In order to remove the 1,1′,1″-phosphoryltripyrrolidine the product is taken up in a little tetrahydrofuran, water is added to the mixture until a precipitate forms, the tetrahydrofuran is removed in vacuo, and the precipitate is collected by suction filtration and dried under high vacuum. 42 mg (65% of theory) of the title compound are obtained.

Workup

  1. customIn order to remove the 1,1′,1″-phosphoryltripyrrolidine the product
  2. additionis added to the mixture until a precipitate forms
  3. customthe tetrahydrofuran is removed in vacuo
  4. filtrationthe precipitate is collected by suction filtration
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-d9a08a8d5d6b482d8b3899e483d058df
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

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