1,2-Dichloroethane → HCID 178487650, compound

HRID 526463Notes

Reaction equation

HRID 526463 reaction equation
C(C1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][N:16]=3)[C:13]=2[OH:14])=[CH:5][CH:4]=1)#N.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CC[N:40](C(C)C)C(C)C.[NH2:47][CH:48]1[CH2:53][CH2:52][N:51](C(OC(C)(C)C)=O)[CH2:50][CH2:49]1.[C:61]([OH:67])(C(F)(F)F)=O>CO.C(Cl)Cl.CC(N(C)C)=O>[OH:14][C:13]1[N:12]([C:15]2[CH:23]=[CH:22][C:18]([C:19]([NH:47][CH:48]3[CH2:49][CH2:50][NH:51][CH2:52][CH2:53]3)=[O:21])=[CH:17][N:16]=2)[N:11]=[CH:10][C:9]=1[C:6]1[CH:5]=[CH:4][N:40]=[C:8]([O:67][CH3:61])[CH:7]=1

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 6422Trifluoroacetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 178509615HCID 178509615, compound

Product 1

HCID 178487650HCID 178487650, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

Combined 6-(4-(4-cyanophenyl)-5-hydroxy-1H-pyrazol-1-yl)nicotinic acid (50 mg, 0.163 mmol), EDC (46.9 mg, 0.245 mmol) and HOBT (37.5 mg, 0.245 mmol) and DMA (1 mL), and treated with Hunig's base (0.114 ml, 0.653 mmol) and stirred at ambient temperature for 5 minutes, then added to 4-amino-1-Boc-piperidine (38.5 mg, 0.327 mmol) and stirred at room temperature overnight. The reaction mixture was then diluted to a total volume of about 1.5 mL with methanol and purified via prep HPLC. The product containing fractions were collected and concentrated in vacuum to give a residue which was treated with TFA (2 mL) in DCM (2 mL). After stirring at ambient temperature overnight the reaction was concentrated in vacuo and dried under vacuum to give the title compound (39.3 mg, 62%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.65-1.82 (m, 2H) 1.93-2.08 (m, 2H) 2.94-3.16 (m, 2H) 3.35 (d, J=12.63 Hz, 2H) 3.99-4.19 (m, 1H) 7.80 (d, J=8.59 Hz, 2H) 8.15 (d, J=7.33 Hz, 2H) 8.29-8.78 (m, 6H) 8.87-8.99 (m, 1H) 13.59 (br. s., 1H). MS m/z [M+H]+ 389.2.

Workup

  1. stirringstirred at room temperature overnight
  2. custompurified via prep HPLC
  3. additionThe product containing fractions
  4. customwere collected
  5. concentrationconcentrated in vacuum
  6. customto give a residue which
  7. stirringAfter stirring at ambient temperature overnight the reaction
  8. concentrationwas concentrated in vacuo
  9. customdried under vacuum

Sources & evidence

ORD record
ord-86eb22b3685246f8aa4d12507a2f7b06
Source dataset
uspto-grants-2016_05
Patent number
US09345713B2

Reaction notes

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