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Cesium carbonate → 4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(1-ethyl-4-piperidyl)-2,5-difluoro-benzamide

HRID 2234316
Notes
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Reaction equation

HRID 2234316 reaction equation
Cl[C:2]1[N:12]=[C:11]2[C:5]([NH:6][C:7](=[O:20])[C:8]([CH3:19])([CH3:18])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.[NH2:21][C:22]1[C:38]([F:39])=[CH:37][C:25]([C:26]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[CH2:31][CH2:30]2)=[O:27])=[C:24]([F:40])[CH:23]=1.[C:41](=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>[Pd+2].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.O1CCOCC1>[CH:13]1([N:10]2[CH2:9][C:8]([CH3:19])([CH3:18])[C:7](=[O:20])[N:6]([CH3:41])[C:5]3[C:11]2=[N:12][C:2]([NH:21][C:22]2[C:38]([F:39])=[CH:37][C:25]([C:26]([NH:28][CH:29]4[CH2:34][CH2:33][N:32]([CH2:35][CH3:36])[CH2:31][CH2:30]4)=[O:27])=[C:24]([F:40])[CH:23]=2)=[N:3][CH:4]=3)[CH2:17][CH2:16][CH2:15][CH2:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 581540122-Chloro-9-cyclopentyl-7,7-dimethyl-5,7,8,9-tetrahydro-pyrimido[4,5-b][1,4]diazepin-6-one2×HCID 686848474-amino-N-(1-ethyl-4-piperidyl)-2,5-difluoro-benzamide2×

Product 1

HCID 68686107
4-[(2-cyclopentyl-4,4,6-trimethyl-5-oxo-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-10-yl)amino]-N-(1-ethyl-4-piperidyl)-2,5-difluoro-benzamide
Yield 54.6%

Reagents, catalysts & solvents 2

HCID 9897284tris(dibenzylideneacetone) palladium (II)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

10-chloro-2-cyclopentyl-4,4-dimethyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-8,10,12-trien-5-one (Intermediate 127; 100 mg, 0.32 mmol), 4-amino-N-(1-ethyl-4-piperidyl)-2,5-difluoro-benzamide (Intermediate 235; 101 mg, 0.36 mmol) and caesium carbonate (22 mg, 0.65 mmol) added to dioxane (5 mL) and the suspension bubbled with nitrogen for 10 minutes. tris(dibenzylideneacetone) palladium (II) (18 mg, 0.02 mmol) and XANTPHOS (17 mg, 0.03 mmol) were added and the mixture heated at 110° C. overnight. The mixture was filtered and the filtrate loaded onto an SCX (10 g) cartridge pre-wet with methanol, washed with methanol and eluted with methanolic ammonia. Product containing fractions were combined and evaporated and the resultant material purified by base modified reverse phase preparative HPLC to yield the title compound as a white crystalline solid (97 mg, 54%).

Workup

  1. customthe suspension bubbled with nitrogen for 10 minutes
  2. filtrationThe mixture was filtered
  3. washwashed with methanol
  4. washeluted with methanolic ammonia
  5. additionProduct containing fractions
  6. customevaporated
  7. customthe resultant material purified by base modified reverse phase preparative HPLC

Sources & evidence

ORD record
ord-ef8721cc84e9428b9152816b27b78891
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709471B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes