Chloride → HCID 178497986, compound

HRID 1092017

Reaction equation

HRID 1092017 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].C(Cl)Cl.[Cl-].[NH2:18][C:19]1[N:23](C(OC(C)(C)C)=O)[N:22]=[C:21]([CH2:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([O:39][CH3:40])[CH:34]=2)[CH:20]=1>CN(C=O)C.C(#N)C.C(O)=O.N1C=CC=CC=1>[CH3:40][O:39][C:35]1[CH:34]=[C:33]([CH2:32][CH2:31][C:21]2[CH:20]=[C:19]([NH:18][C:11]([C:8]3[N:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=3)=[O:13])[NH:23][N:22]=2)[CH:38]=[CH:37][CH:36]=1

Participants

9

Reactant 4

HCID 312ChlorideHCID 6344DichloromethaneHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 57440385Tert-butyl 5-amino-3-[2-(3-methoxyphenyl)ethyl]pyrazole-1-carboxylate

Product 1

HCID 178497986HCID 178497986, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 284Formic AcidSolventHCID 1049PyridineSolventHCID 6342AcetonitrileSolvent

Procedure

5-Methoxycarbonylpyridine-2-carboxylic acid (0.285 g, 1.58 mmol) was added to DCM (40 ml), to this was added oxayl chloride (0.165 ml, 1.90 mmol) and a few drops of anhydrous DMF. The reaction mixture was stirred for 30 mins before the addition of tert-butyl 5-amino-3-[2-(3-methoxyphenyl)ethyl]pyrazole-1-carboxylate (0.50 g, 1.58 mmol) and pyridine (2.0 ml). The reaction was stirred overnight. The reaction was evaporated to dryness to give yield to a gum. To this gum was added formic acid. The reaction mixture was stirred for 1 h before being evaporated to dryness. The resulting gum was quenched with saturated potassium carbonate (30 ml), extracted with DCM (3×50 ml), dried (MgSO4) and the solvent removed in vacuo to yield a viscous gum. Trituration with acetonitrile gave the desired product as a slightly yellow solid (24 mg, 4%); 1H NMR (400.132 MHz, DMSO) δ 2.92 (s, 4H), 3.74 (s, 3H), 3.95 (s, 3H), 6.50 (s, 1H), 6.76 (d, 1H), 6.83-6.82 (m, 2H), 7.20 (t, 1H), 8.26 (d, 1H), 8.53 (d, 1H), 9.17 (s, 1H), 10.38 (s, 1H), 12.31 (s, 1H); MH+381.

Workup

  1. customThe reaction was evaporated to dryness
  2. customto give
  3. customyield to a gum
  4. stirringThe reaction mixture was stirred for 1 h
  5. custombefore being evaporated to dryness
  6. customThe resulting gum was quenched with saturated potassium carbonate (30 ml)
  7. extractionextracted with DCM (3×50 ml)
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo
  10. customto yield a viscous gum

Sources & evidence

ORD record
ord-d1844e8730d445318e371f35b4c9f4c9
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Linked notes

Loading…