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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-Fluoro-pyridine-2-carboxylic acid isobutyl-(8-propyl[1,2,4]triazolo-[1,5-c]pyrimidin-7-ylmethyl)-amide

HRID 898709
Notes
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Reaction equation

HRID 898709 reaction equation
[CH2:1]([NH:5][CH2:6][C:7]1[N:12]=[CH:11][N:10]2[N:13]=[CH:14][N:15]=[C:9]2[C:8]=1[CH2:16][CH2:17][CH3:18])[CH:2]([CH3:4])[CH3:3].[F:19][C:20]1[N:25]=[C:24]([C:26](O)=[O:27])[CH:23]=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:1]([N:5]([CH2:6][C:7]1[N:12]=[CH:11][N:10]2[N:13]=[CH:14][N:15]=[C:9]2[C:8]=1[CH2:16][CH2:17][CH3:18])[C:26]([C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([F:19])[N:25]=1)=[O:27])[CH:2]([CH3:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 2260276-Fluoropyridine-2-carboxylic acidHCID 58661548Isobutyl-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-amine

Product 1

HCID 586615556-Fluoro-pyridine-2-carboxylic acid isobutyl-(8-propyl[1,2,4]triazolo-[1,5-c]pyrimidin-7-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of isobutyl-(8-propyl-[1,2,4]triazolo[1,5-c]pyrimidin-7-ylmethyl)-amine (2.8 mmol) and 6-fluoro-pyridine-2-carboxylic acid (0.47g, 3.34 mmol) in DCM (10 ml) is added EDCI (0.61 g) and DMAP (0.153 g). The mixture is stirred at room temperature overnight. DCM (10 ml) is added to dilute the mixture. The mixture is washed with water (5 mL), dried (Na2SO4) and solvent evaporated. Preparative TLC purification of the residue (2:1 of hexane: ethyl acetate) provides the title product. H1 NMR δ (CDCl3) (mixture of rotamers) 9.25 (s, 0.51), 9.18 (s, 0.5H), 8.39 (s, 0.5H), 8.36 (s, 0.5H), 7.78-7.93 (m, 1H), 7.68 (d, 0.5H), 7.57 (d, 0.5H), 6.99 (d, 0.5H), 6.92 (d, 0.5H), 5.03 (s, 1H), 4.89 (s, 1H), 3.52 (d, 1H), 3.35 (d, 1H), 3.12 (t, 1H), 2.83 (t, 1H), 1.95-2.20 (m, 1H), 1.59-1.85 (m, 2H), 0.88-1.10 (m, 6H), 0.82 (t, 3H).

Workup

  1. additionto dilute the mixture
  2. washThe mixture is washed with water (5 mL)
  3. dry with materialdried (Na2SO4) and solvent
  4. customevaporated
  5. customPreparative TLC purification of the residue (2:1 of hexane: ethyl acetate)

Sources & evidence

ORD record
ord-72c8224fb15540dda471c9cc897f6e79
Source dataset
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07351826B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes