1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874481, compound

HRID 1093792Notes

Reaction equation

HRID 1093792 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([N:17]2[CH:21]=[C:20]([C:22]([OH:24])=O)[N:19]=[N:18]2)[CH:14]=[N:15][CH:16]=1.NC1C=NC=C(F)C=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:55][CH2:56][C:57]([N:59]1[CH2:64][CH2:63][CH:62]([O:65][C:66]2[CH:71]=[CH:70][CH:69]=[CH:68][C:67]=2[Cl:72])[CH2:61][CH2:60]1)=[O:58]>CN(C=O)C.O>[Cl:72][C:67]1[CH:68]=[CH:69][CH:70]=[CH:71][C:66]=1[O:65][CH:62]1[CH2:61][CH2:60][N:59]([C:57](=[O:58])[CH2:56][NH:55][C:22]([C:20]2[N:19]=[N:18][N:17]([C:13]3[CH:14]=[N:15][CH:16]=[C:11]([F:10])[CH:12]=3)[CH:21]=2)=[O:24])[CH2:64][CH2:63]1

Participants

9

Reactant 6

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 5744505-Fluoro-3-pyridinamineHCID 665915282-Amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochlorideHCID 665917781-(5-Fluoro-3-pyridinyl)-1H-1,2,3-triazole-4-carboxylic acid

Product 1

HCID 57874481HCID 57874481, compoundYield 90.74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (195 mg, 1.66 mmol) was added to a stirred solution of 1-(5-fluoro-pyridin-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid (70 mg, 0.33 mmol) (prepared by the method used for the synthesis of Intermediate 64, starting from 3-amino-5-fluoropyridine) in DMF (5 mL) followed by HOBt (55 mg, 0.41 mmol) and EDCI (177 mg, 0.92 mmol). After 2 minutes of stirring, 2-amino-1-[4-(2-chloro-phenoxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (124 mg, 0.4 mmol) was added and the resulting mixture was stirred at ambient temperature overnight. Cold water was then added and the solid was collected to afford 147 mg (90.74% Yield) of 1-(5-fluoro-pyridin-3-yl)-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(2-chloro-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 441 (M+1), 98.31%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 9.24 (d, 1H), 8.76 (d, 1H), 8.56 (t, 1H), 8.46 (d, 1H), 7.74 (d, 1H), 7.48 (d, 1H), 7.36 (q, 2H), 7.02 (t, 1H), 4.8 (m, 1H), 4.4 (d, 2H), 3.8 (t, 2H), 3.6 (t, 2H), 2.1 (d, 2H), 1.8 (d, 2H).

Workup

  1. customprepared by the method
  2. additionwas added
  3. stirringthe resulting mixture was stirred at ambient temperature overnight
  4. customthe solid was collected

Sources & evidence

ORD record
ord-834f08c6d349414f94e9a77bc8a0234d
Source dataset
uspto-grants-2012_03
Patent number
US08129376B2

Reaction notes

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