Pyridine → HCID 91490121, compound

HRID 2086592Notes

Reaction equation

HRID 2086592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[N:19]=1)([OH:17])[CH2:13]2.[C:32]([NH:39][CH2:40][CH2:41][NH2:42])([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].N1C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:31])[N:9]1[CH:14]2[CH2:15][CH2:16][CH:10]1[CH2:11][C:12]([C:18]1[N:19]=[C:20]([NH:42][CH2:41][CH2:40][NH:39][C:32](=[O:33])[O:34][C:35]([CH3:37])([CH3:36])[CH3:38])[CH:21]=[CH:22][CH:23]=1)([OH:17])[CH2:13]2

Participants

4

Reactant 3

HCID 1049PyridineHCID 187201N-BOC-ethylenediamine2×HCID 22725086HCID 22725086, compound

Product 1

HCID 91490121HCID 91490121, compound

Procedure

Stir a solution of the product from Step 1 (64.5 mg, 0.128 mmol), N-Boc-ethylenediamine (123 mg, 0.77 mmol) and pyridine (12 mg, 0.154 mmol) at 110° C. in a sealed tube for 3.5 h. Cool to RT, add N-Boc-ethylenediamine (0.3 ml) and heat at 140° C. overnight. Cool to RT, quench the reaction with H2O, extract with EtOAc, dry and concentrate. Purify the residue by column chromatography to give the desired product.

Workup

  1. temperatureheat at 140° C. overnight
  2. temperatureCool to RT
  3. customquench
  4. customthe reaction with H2O
  5. extractionextract with EtOAc
  6. customdry
  7. concentrationconcentrate
  8. customPurify the residue by column chromatography

Sources & evidence

ORD record
ord-9f2b9949c9f34e64ada13b55277b9b7c
Source dataset
uspto-grants-2004_04
Patent number
US06727254B2

Reaction notes

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