1,2-Dichloroethane → HCID 16660147, compound

HRID 1362347Notes

Reaction equation

HRID 1362347 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[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:40].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[O:36][C:37]3[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=3[C:39]=2[CH3:40])=[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 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 66967081HCID 66967081, compound

Product 1

HCID 16660147HCID 16660147, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

EDC (98 mg, 0.51 mmol) was added to a suspension of 3-[6-Amino-5-(1-hydroxy-1-methyl-ethyl)-pyridin-3-yl]-acrylic acid hydrochloride (110 mg, 0.43 mmol), HOBt (63 mg, 0.47 mmol), methyl-(3-methyl-benzofuran-2-ylmethyl)-amine (110 mg, 0.47 mmol) and (i-Pr)2EtN (0.36 mL, 2.1 mmol) in DMF (7 mL). The mixture was allowed to stir overnight at 40° C. The mixture was cooled to 0° C. and diluted with H2O (60 mL) with rapid stirring. Only a small amount of precipitate was formed, therefore the product was extracted using EtOAc (2×50 mL), the combined organic layers washed with brine (60 mL), dried over MgSO4 and dried under high vacuum. The solid was then subjected to flash chromatography on silica gel using 10% methanol:dichloromethane. Yield: 77.6 mg (48%); 1H NMR (300 MHz, DMSO-d6) δ 8.13 (s, 1H), 7.70 (s, 1H), 7.58 (d, J=7.9 Hz, 1H), 7.50 (d, J=7.6 Hz, 1H), 7.44 (s, 1H), 7.23-7.32 (m, 2H), 6.98 (d, J=17.7 Hz, 1H), 6.59 (s, 2H), 5.51 (s, 1H), 5.00 and 4.80 (2×s, 2H), 3.20 and 2.99 (2×s, 3H), 2.28 (s, 3H), 1.54 (s, 6H); ESI MS m/z 380.2 [C22H25N3O3+H]+

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. customOnly a small amount of precipitate was formed
  3. extractionthe product was extracted
  4. washthe combined organic layers washed with brine (60 mL)
  5. dry with materialdried over MgSO4
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-d2ddd692ce4f44a89147ba79794ff32b
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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