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Diisopropylethylamine → HCID 68681610, Verbindung

HRID 2234519
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2234519
[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:12])[CH:3]=1.[N:13]1([CH2:18][C:19]2([CH2:22][NH2:23])[CH2:21][CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CO>[NH2:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6]([NH:23][CH2:22][C:19]2([CH2:18][N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[CH2:20][CH2:21]2)=[O:8])=[C:4]([F:12])[CH:3]=1
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Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 201514774-Amino-2,5-difluorobenzoic acidHCID 28064766(1-(Pyrrolidin-1-ylmethyl)cyclopropyl)methanamine2×

Produkt 1

HCID 68681610HCID 68681610, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-amino-2,5-difluoro-benzoic acid (Rare Chemicals GmbH; 700 mg, 4.04 mmol), [1-(pyrrolidin-1-ylmethyl)cyclopropyl]methanamine (Intermediate 33; 655 mg, 4.25 mmol), HATU (1.69 g, 4.44 mmol) and DIPEA (2.1 mL, 12.12 mmol) were combined in DMF (10 mL) and stirred at room temperature for 2 hours. The reaction mixture divided into two portions and each loaded on to an SCX-2 column (20 g) pre-wet with MeOH (2 column volumes), flushed with MeOH (2 column volumes) and eluted with 2M ammonia in MeOH. Product containing fractions were evaporated and the residue taken up in DCM and purified on a silica column eluting with a 0-5% gradient of 2M ammonia in MeOH/DCM then 5% 2M ammonia in MeOH/DCM. Fractions containing product were combined and evaporated to yield the title compound as an orange gum which solidified on standing to an orange solid (472 mg, 38%)

Aufarbeitung

  1. customflushed with MeOH (2 column volumes)
  2. washeluted with 2M ammonia in MeOH
  3. additionProduct containing fractions
  4. customwere evaporated
  5. custompurified on a silica column
  6. washeluting with a 0-5% gradient of 2M ammonia in MeOH/DCM
  7. additionFractions containing product
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6217f409257a46539f45298651bac0f7
Quelldatensatz
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07709471B2

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