Diisopropylethylamine → HCID 44230250, compound

HRID 1949328Notes

Reaction equation

HRID 1949328 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:10]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=3)=[CH:13][C:12]([C:23]([OH:25])=O)=[N:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].C(N(CC)C(C)C)(C)C.ClC1C=C(N2C(C3C=CC=C(OCCO)C=3)=CC(C([N:59]3[CH2:63][C:62](=[O:64])[NH:61][CH2:60]3)=O)=N2)C=CC=1>C(O)=O>[C:21]([C:17]1[CH:16]=[C:15]([C:14]2[N:10]([C:5]3[CH:6]=[CH:7][C:8]([F:9])=[C:3]([C:1]#[N:2])[CH:4]=3)[N:11]=[C:12]([C:23]([N:59]3[CH2:63][C:62](=[O:64])[NH:61][CH2:60]3)=[O:25])[CH:13]=2)[CH:20]=[CH:19][CH:18]=1)#[N:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 58277360HCID 58277360, compoundHCID 58277377HCID 58277377, compound

Product 1

HCID 44230250HCID 44230250, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The preparation of the title compound takes place starting from the compound of Example 112A 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. 25 mg (48% 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-5efa5ae11a064da29918b520caebb800
Source dataset
uspto-grants-2013_03
Patent number
US08399682B2

Reaction notes

Loading…