Cesium carbonate → HCID 131734502, compound

HRID 590883Notes

Reaction equation

HRID 590883 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]2[C:8]([N:30]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1.[C:49](=[O:56])([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[NH2:50].CC(C1C=C(C(C)C)C(C2C(P(C3CCCCC3)C3CCCCC3)=C(OC)C=CC=2OC)=C(C(C)C)C=1)C.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1>[C:52]([O:51][C:49](=[O:56])[NH:50][C:2]1[N:7]=[CH:6][C:5]2[C:8]([N:30]([CH2:40][C:41]3[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=3)[CH2:31][C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)=[N:9][N:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:4]=2[CH:3]=1)([CH3:55])([CH3:54])[CH3:53]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 25112535BrettphosHCID 118271676HCID 118271676, compound

Product 1

HCID 131734502HCID 131734502, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Under inert atmosphere, to a solution of 6-chloro-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridin-3-amine (0.5 g, 0.77 mmol) in anhydrous 1,4-dioxane (10.0 mL) was added tert-Butyl carbamate (0.26 g, 2.3 mmol), brettphos pre catalyst (0.03 g, 0.004 mmol), Cs2CO3 (0.75 g, 2.3 mmol) and the contents were heated in a sealed tube at 100° C. After 6 h, the reaction mixture was brought back to ambient temperature and the volatiles were removed under reduced pressure. The residue thus obtained was purified by a flash column chromatography to afford the title compound (0.4 g, 71% yield). MS ES calc'd. for C46H45N5O4 [M+H]+ 732. Found 732.

Workup

  1. customwas brought back to ambient temperature
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified by a flash column chromatography

Sources & evidence

ORD record
ord-d087bf9f131d457b82b7f39d0e41c919
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

Loading…