1,2-Dichloroethane → HCID 16660149, compound

HRID 1362349Notes

Reaction equation

HRID 1362349 reaction equation
C(Cl)CCl.Cl.[NH2:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([OH:17])=O)=[CH:9][C:8]=1[C:18]([OH:21])([CH3:20])[CH3:19].C1C=CC2N(O)N=NC=2C=1.[CH3:32][NH:33][CH2:34][C:35]1[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=2[O:37][C:36]=1[CH3:44].C(N(C(C)C)C(C)C)C>CN(C=O)C.O>[NH2:6][C:7]1[N:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([N:33]([CH3:32])[CH2:34][C:35]2[C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][C:38]=3[O:37][C:36]=2[CH3:44])=[O:17])=[CH:9][C:8]=1[C:18]([OH:21])([CH3:20])[CH3:19]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66967079HCID 66967079, compoundHCID 66967084Methyl(2-methylbenzofuran-3-ylmethyl)amine

Product 1

HCID 16660149HCID 16660149, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (0.13 g, 0.70 mmol) was added to a suspension of (E)-3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-acrylic acid hydrochloride (0.15 g, 0.58 mmol), HOBt (0.09 g, 0.64 mmol), methyl-(2-methyl-benzofuran-3-ylmethyl)-amine (0.11 g, 0.64 mmol) and (i-Pr)2EtN (0.60 mL, 2.48 mmol) in DMF (6 mL). The mixture was allowed to stir overnight at room temperature. The mixture was cooled to 0° C. and diluted with H2O (15 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (20 mL) then dried under high vacuum. The solid was then triturated with Et2O, and the resultant beige solid was collected, to yield 160 mg (73%) of product. 1H NMR (300 MHz, DMSO-d6) δ 8.14 (s, 1H), 7.67-7.47 (m, 4H), 7.26-6.99 (m, 3H), 6.58 (s, 2H), 5.49 (s, 1H), 4.80 and 4.74 (2×s, 2H), 3.04 and 2.85 (2×s, 3H), 2.52 (s, 3H), 1.53 (s, 6H); ESI MS m/z 380 [C22H25N3O3+H]+

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O (20 mL)
  4. customthen dried under high vacuum
  5. customThe solid was then triturated with Et2O
  6. customthe resultant beige solid was collected

Sources & evidence

ORD record
ord-3faa67943f9f48638d54168583f01e5b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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