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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 57874477, compound

HRID 1093839
Notes
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Reaction equation

HRID 1093839 reaction equation
CCN(C(C)C)C(C)C.[F:10][C:11]1[CH:12]=[C:13]([N:18]2[CH:22]=[C:21]([C:23]([OH:25])=O)[N:20]=[N:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH2:48][CH2:49][C:50]([N:52]1[CH2:57][CH2:56][CH:55]([O:58][C:59]2[CH:60]=[N:61][CH:62]=[C:63]([Cl:65])[CH:64]=2)[CH2:54][CH2:53]1)=[O:51]>CN(C=O)C.O>[Cl:65][C:63]1[CH:64]=[C:59]([O:58][CH:55]2[CH2:54][CH2:53][N:52]([C:50](=[O:51])[CH2:49][NH:48][C:23]([C:21]3[N:20]=[N:19][N:18]([C:13]4[CH:14]=[C:15]([F:17])[CH:16]=[C:11]([F:10])[CH:12]=4)[CH:22]=3)=[O:25])[CH2:57][CH2:56]2)[CH:60]=[N:61][CH:62]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 287431861-(3,5-difluorophenyl)-1H-1,2,3-triazole-4-carboxylic acidHCID 665916722-Amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride

Product 1

HCID 57874477
HCID 57874477, compound
Yield 54.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIPEA (149.2 mg, 1.15 mmol) was added to a stirred solution of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid (65 mg, 0.28 mmol) in DMF (2 mL) followed by HOBt (43 mg, 0.31 mmol) and EDCI (110 mg, 0.57 mmol). After 2 minutes of stirring, 2-amino-1-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-ethanone hydrochloride (prepared according to Step 1 and 5 of the General Scheme) (88.4 mg, 0.28 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was added and the precipitate was collected. The crude solid was purified by recrystallisation from a mixture of DCM and hexane to afford 95 mg (54.4% Yield) of 1-(3,5-difluoro-phenyl)-1H-[1,2,3]triazole-4-carboxylic acid {2-[4-(5-chloro-pyridin-3-yloxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 477.12, 98.45%. 1H NMR (300 MHz, DMSO-d6): δ 9.5 (s, 1H), 8.5 (t, 1H), 8.3 (d, 1H), 8.2 (d, 1H), 7.9 (d, 2H), 7.75 (t, 1H), 7.58-7.5 (m, 1H), 4.8 (m, 1H), 4.2 (d, 2H), 4.0-3.8 (m, 1H), 3.8-3.6 (m, 1H), 3.4 (m, 1H), 3.2 (m, 1H), 2.1-1.9 (m, 2H), 1.9-1.5 (m, 2H).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. customthe precipitate was collected
  4. customThe crude solid was purified by recrystallisation from a mixture of DCM and hexane

Sources & evidence

ORD record
ord-83e300a1dc684632804cdecb1e9e8bb1
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129376B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes