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Triethylamine → (1H-benzo[d]imidazol-4-yl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

HRID 1908176
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Reaktionsgleichung

Reaktionsgleichung von HRID 1908176
[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[O:13][C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:5]=2[CH:4]=[N:3]1.[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29](O)=[O:30])[C:23]=2[N:22]=[CH:21]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH-].[Na+]>ClCCl>[NH:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]([N:17]3[CH2:18][CH2:19][C:14]4([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[C:6]=5[C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=5[O:13]4)[CH2:15][CH2:16]3)=[O:30])[C:23]=2[N:22]=[CH:21]1
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Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 27717581H-benzimidazole-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 585507381-Methylspiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]

Produkt 1

HCID 58550819
(1H-benzo[d]imidazol-4-yl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]-1'-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (211 mg, 0.830 mmol), 1H-benzimidazole-4-carboxylic acid (134 mg, 0.830 mmol) and triethylamine (346 μL, 2.50 mmol) in dichloromethane (2 mL) was added HATU (314 mg, 0.830 mmol) in one portion and the mixture was stirred for 12 hours. The reaction mixture was treated with 1M NaOH (1 mL) for 10 minutes. Dichloromethane (5 mL) was added. The two layers were separated and the aqueous layer was extracted with dichloromethane (2×5 mL). The organic layers were combined, washed with brine, dried over MgSO4, filtered and evaporated to yield a residue that was purified on silica using a gradient of 0.5-30% MeOH in dichloromethane to yield (1H-benzo[d]imidazol-4-yl)(1-methyl-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-yl)methanone. ESI-MS m/z calc. 399.5. found 400.5 (M+1)+. Retention time: 1.12 minutes (4 min run).

Aufarbeitung

  1. customThe two layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (2×5 mL)
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto yield a residue that
  8. customwas purified on silica using a gradient of 0.5-30% MeOH in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-00f1f4a64661484fa01423c7f84c00d4
Quelldatensatz
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08598164B2

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