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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-Butyl 4-({[(2-chloro-5-fluoropyridin-3-yl)carbonyl]amino}methyl)benzoate

HRID 1293175
Notes
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Reaction equation

HRID 1293175 reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][CH2:13][C:14]1[CH:26]=[CH:25][C:17]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>ClCCl.O.C(N(CC)CC)C>[Cl:1][C:2]1[C:3]([C:4]([NH:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])=[CH:25][CH:26]=2)=[O:6])=[CH:7][C:8]([F:11])=[CH:9][N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 114352432-Chloro-5-fluoronicotinic acidHCID 14514888tert-Butyl 4-(aminomethyl)benzoate

Product 1

HCID 86627076tert-Butyl 4-({[(2-chloro-5-fluoropyridin-3-yl)carbonyl]amino}methyl)benzoateYield 82%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 2-chloro-5-fluoronicotinic acid (2.0 g, 10 mmol) and tert-butyl 4-(aminomethyl)benzoate (1.65 g, 8 mmol) in dichloromethane (25 mL) were successively added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (2.88 g, 15 mmol), 1-hydroxybenzotriazole hydrate (HOBT) (1.53 g, 10 mmol), and triethylamine (5 mL). After being stirred overnight, the reaction mixture was poured into water (100 mL). The organic layer_was separated and the aqueous layer was extracted with dichloromethane (50 mL×2). The combined organic layers were washed with brine (100 mL), dried (sodium sulfate), and evaporated. The residue was purified by flush column chromatography on silica gel (200 g) eluting with dichloromethane/ethyl acetate (20/1) to afford 2.39 g (82%) of the title compounds as white solids: 1H-NMR (CDCl3) δ 8.33 (1H, d, J=3.1 Hz), 7.97 (2H, d, J=8.4 Hz), 7.91 (1H, dd, J=7.9, 3.1 Hz), 7.40 (2H, d, J=8.4 Hz), 7.04 (1H, br.s), 4.70 (2H, d, J=5.9 Hz), 1.58 (9H, s).

Workup

  1. customThe organic layer_was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (50 mL×2)
  3. washThe combined organic layers were washed with brine (100 mL)
  4. dry with materialdried (sodium sulfate)
  5. customevaporated
  6. customThe residue was purified
  7. customby flush column chromatography on silica gel (200 g)
  8. washeluting with dichloromethane/ethyl acetate (20/1)

Sources & evidence

ORD record
ord-89aaa8a8182a4f408492dd3223c26f51
Source dataset
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07238714B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes