3-Aminopyridine → HCID 57874416, compound

HRID 1093880Notes

Reaction equation

HRID 1093880 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]2[CH:41]=[C:40]([C:42]([NH:44][CH2:45][C:46]([OH:48])=O)=[O:43])[N:39]=[N:38]2)[CH:32]=1.NC1C=NC=CC=1.Cl.[Cl:57][C:58]1[CH:69]=[CH:68][CH:67]=[CH:66][C:59]=1[O:60][CH:61]1[CH2:65][CH2:64][NH:63][CH2:62]1>CN(C=O)C>[Cl:57][C:58]1[CH:69]=[CH:68][CH:67]=[CH:66][C:59]=1[O:60][CH:61]1[CH2:65][CH2:64][N:63]([C:46](=[O:48])[CH2:45][NH:44][C:42]([C:40]2[N:39]=[N:38][N:37]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)[CH:41]=2)=[O:43])[CH2:62]1

Participants

8

Reactant 6

HCID 100093-AminopyridineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 450754773-(2-Chlorophenoxy)pyrrolidine hydrochlorideHCID 66592012[(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid

Product 1

HCID 57874416HCID 57874416, compoundYield 43.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

DIPEA (167 mg, 1.3 mmol) followed by HOBt (48 mg, 0.35 mmol) and EDCI (124 mg, 0.64 mmol) were added to a stirred solution of [(1-pyridin-3-yl-1H-[1,2,3]triazole-4-carbonyl)-amino]-acetic acid (prepared by the method used for the synthesis of Intermediate 64, starting from 3-aminopyridine, and subsequently, application of Step 3 of the General Scheme) (80 mg, 0.32 mmol) in DMF (2 mL). After 2 minutes of stirring, 3-(2-chloro-phenoxy)-pyrrolidine hydrochloride (prepared by the method used for the synthesis of Intermediate 72) (75.7 mg, 0.32 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction mixture was partitioned between cold water and ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. Purification by recrystallisation from a mixture of DCM and hexane afforded 60 mg (43.4% Yield) of 1-pyridin-3-yl-1H-[1,2,3]triazole-4-carboxylic acid {2-[3-(2-chloro-phenoxy)-pyrrolidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 427. 1H NMR (300 MHz, DMSO-d6): δ 9.45 (s, 1H), 9.2 (d, 1H), 8.75 (d, 1H), 8.6 (q, 1H), 8.4 (m, 1H), 7.7 (q, 1H), 7.5-7.4 (m, 1H), 7.4-7.2 (m, 2H), 7.06-6.96 (m, 1H), 5.3-5.1 (d, 1H), 4.25-4.0 (m, 2H), 4.0-3.6 (m, 4H), 3.5-3.4 (m, 1H), 2.3-2.2 (m, 1H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at room temperature overnight
  4. customThe reaction mixture was partitioned between cold water and ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customby recrystallisation
  9. additionfrom a mixture of DCM and hexane

Sources & evidence

ORD record
ord-6ec6266ffbe44435bd158a8fac9c97e7
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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