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1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-[4-(2-Chloroethyl)phenyl]-5,7-dimethyl-2-[2-(1,3-thiazol-2-yl)ethyl]-3H-imidazo[4,5-b]pyridine

HRID 724035
Notes
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Reaction equation

HRID 724035 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:16]([NH2:17])=[C:15]([CH3:18])[CH:14]=[C:13]([CH3:19])[N:12]=2)=[CH:6][CH:5]=1.[S:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH2:25][CH2:26][C:27](O)=O.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[Cl:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:11]3=[N:12][C:13]([CH3:19])=[CH:14][C:15]([CH3:18])=[C:16]3[N:17]=[C:27]2[CH2:26][CH2:25][C:21]2[S:20][CH:24]=[CH:23][N:22]=2)=[CH:6][CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27606093-(2-Thiazolyl)propionic acidHCID 69961874N2-[4-(2-Chloroethyl)phenyl]-4,6-dimethyl-2,3-pyridinediamine

Product 1

HCID 218757313-[4-(2-Chloroethyl)phenyl]-5,7-dimethyl-2-[2-(1,3-thiazol-2-yl)ethyl]-3H-imidazo[4,5-b]pyridineYield 53%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a mixture of N2-[4-(2-chloroethyl)phenyl]-4,6-dimethyl-2,3-pyridinediamine (step 2, 276 mg, 1.0 mmol) and 3-(1,3-thiazol-2-yl)propanoic acid (157 mg, 1.0 mmol) in dichloromethane (10 mL) was added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, hydrochloride (WSC) (192 mg, 1.0 mmol) in one portion. The reaction mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure. The residue was suspended in toluene (20 mL) and heated at 150° C. for 5 h. The reaction mixture was poured into water (50 mL), the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic phases were washed with brine (50 mL) and dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to afford 210 mg (53%) of the title compound: MS (EI) m/z 396 (M+); 1H-NMR (CDCl3) δ 7.63 (1H, d, J=3.4 Hz), 7.39 (2H, d, J=8.3 Hz), 7.28 (2H, d, J=8.3 Hz), 7.15 (1H, d, J=3.4 Hz), 6.93 (1H, s), 3.78 (2H, t, J=7.4 Hz), 3.69–3.50 (2H, m), 3.39–3.20 (2H, m), 3.15 (2H, t, J=7.4 Hz), 2.66 (3H, s), 2.53 (3H, s).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. temperatureheated at 150° C. for 5 h
  3. additionThe reaction mixture was poured into water (50 mL)
  4. customthe organic phase was separated
  5. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  6. washThe combined organic phases were washed with brine (50 mL)
  7. dry with materialdried (Na2SO4)
  8. customAfter removal of solvent
  9. customthe crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-35a5cd6f32044a64aa760d5327e68c17
Source dataset
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07141580B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes