Triethylamine → HCID 67314611, compound

HRID 1011897Notes

Reaction equation

HRID 1011897 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[C:18]([C:22](O)=[O:23])[N:19]([CH3:21])[N:20]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH2:37]([N:39]([CH2:45][CH3:46])[CH:40]1[CH2:44][CH2:43][NH:42][CH2:41]1)[CH3:38].CCN(CC)CC>CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[CH:17]=[C:18]([C:22]([N:42]2[CH2:43][CH2:44][CH:40]([N:39]([CH2:45][CH3:46])[CH2:37][CH3:38])[CH2:41]2)=[O:23])[N:19]([CH3:21])[N:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 199619953-(Diethylamino)pyrrolidineHCID 673151845-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid

Product 1

HCID 67314611HCID 67314611, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 0.124 g (0.39 mmol) of 5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazole-3-carboxylic acid in 1.28 ml of DMF was treated with 0.063 g (0.39 mmol) of CDI. After 4 h, 0.055 g (0.39 mmol) of 3-(diethylamino)pyrrolidine and 0.217 ml (1.56 mmol) of Et3N in 1.28 ml of DMF were added and stirring was continued for 2 h. The solution was partitioned between aqueous saturated NaHCO3/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl, dried (Na2SO4) and evaporated. The crude product was crystallized with Et2O/pentane to give 0.130 g (75%) of [5-(3-benzofuran-2-yl-phenyl)-2-methyl-2H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone as light pink powder. MS: 443.2 (MH+).

Workup

  1. waitwas continued for 2 h
  2. customThe solution was partitioned between aqueous saturated NaHCO3/Et2O (3×)
  3. washThe organic phases were washed with aqueous saturated NaHCO3 and aqueous 10% NaCl
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was crystallized with Et2O/pentane

Sources & evidence

ORD record
ord-bc744af31c9d401dab8f4352b95238ec
Source dataset
uspto-grants-2011_07
Patent number
US07977358B2

Reaction notes

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