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2-amino-4-chloro-N-(5-chloropyridin-2-yl)benzamide → 2-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide

HRID 644183
Notes
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Reaction equation

HRID 644183 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:11]=2[NH2:17])=[N:6][CH:7]=1.[C:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[C:25]([O:32][CH:33]2[CH2:38][CH2:37][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:35][CH2:34]2)[CH:24]=1)([CH3:22])([CH3:21])[CH3:20]>N1C=CC=CC=1.ClCCl>[C:19]([C:23]1[CH:31]=[CH:30][C:26]([C:27]([NH:17][C:11]2[CH:12]=[C:13]([Cl:16])[CH:14]=[CH:15][C:10]=2[C:9]([NH:8][C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=2)=[O:18])=[O:28])=[C:25]([O:32][CH:33]2[CH2:34][CH2:35][N:36]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:37][CH2:38]2)[CH:24]=1)([CH3:22])([CH3:20])[CH3:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 219061992-amino-4-chloro-N-(5-chloropyridin-2-yl)benzamideHCID 866102604-tert-butyl-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride

Product 1

HCID 685368592-[4-(tert-Butyl)-2-(1-Boc-piperidin-4-yloxy)benzoylamino]-N-(5-chloropyridin-2-yl)-4-chlorobenzamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent
HCID 6344
Dichloromethane
Solvent
2×

Procedure

To a stirring solution of N-(5-chloropyridin-2-yl)-2-amino-4-chlorobenzamide (0.74 g, 26.5 mmol) in pyridine (1 mL) and dichloromethane (20 mL) at 0° C. was added a solution of 4-(tert-butyl)-2-(1-Boc-piperidin-4-yloxy)benzoyl chloride (1.05 g, 26.5 mmol) in dichloromethane (10.5 mL). The cold bath was then removed and after 72 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed with water, followed by satd aq NaHCO3 and then brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo. The residue was chromatographed over silica gel, eluting with a solution of 20% ethyl acetate in hexanes.

Workup

  1. customThe cold bath was then removed and after 72 h
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was then dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed over silica gel
  9. washeluting with a solution of 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-90f705cff8e747bb95815b19c7abeb71
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700628B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes