1,2-Dichloroethane → N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

HRID 340832Notes

Reaction equation

HRID 340832 reaction equation
C(Cl)CCl.Cl.[N:6]1[C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=[C:8]([C:17](=[CH2:21])C(O)=O)[CH:7]=1.C1C=CC2N([OH:31])N=NC=2C=1.CNC[C:35]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1C.[CH2:45]([N:47]([CH:51](C)C)[CH:48]([CH3:50])C)C>CN(C=O)C.O>[CH3:51][N:47]([CH2:48][C:50]1[O:36][C:37]2[CH:44]=[CH:43][CH:42]=[CH:41][C:38]=2[C:39]=1[CH3:35])[C:45](=[O:31])[CH:21]=[CH:17][C:8]1[CH:7]=[N:6][C:11]2[NH:12][CH2:13][CH2:14][O:15][CH2:16][C:10]=2[CH:9]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 131732087HCID 131732087, compound

Product 1

HCID 68413589N-Methyl-N-(3-methyl-benzofuran-2-ylmethyl)-3-(5,7,8,9-tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl)-acrylamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
35 °C

Procedure

EDC (0.10 g, 0.52 mmol) was added to a solution of 3-(5,7,8,9-Tetrahydro-6-oxa-1,9-diaza-benzocyclohepten-3-yl-acrylic acid hydrochloride (0.11 g, 0.43 mmol), HOBt (64 mg, 0.47 mmol), Methyl-(3-methyl-benzofuran-2-ylmethyl)-amine (91 mg, 0.52 mmol) and (i-Pr)2EtN (0.44 mL, 2.58 mmol) in DMF (6 mL). The mixture was allowed to stir overnight at 35° C. lire mixture was cooled to 0° C. and diluted with H2O (15 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (30 mL) then dried under high vacuum. The solid was triturated with Et2O (3.0 mL), stirred for 20 mm then filtered to give a beige solid as a mixture of amide rotaruers. Yield: 0.10 g (62%); 1H NMR (300 MHz, DMSO-d6) δ8.25 (s, 1H), 7.94 (s, 1H), 7.59-7.03 (m, 6H), 6.79 (hr s, 1H), 4.98 and 4.79 (2×s, 2H), 4.53 (s, 2H), 3.77-3.73 (m, 2H), 3.25-3.19 (m, 2H), 3.17 and 2.93 (2×s, 3H), 2.28 (s, 3H); ESI MS m/z 378 [C22H23N3O3+H]+

Workup

  1. temperaturewas cooled to 0° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with H2O (30 mL)
  4. customthen dried under high vacuum
  5. customThe solid was triturated with Et2O (3.0 mL)
  6. stirringstirred for 20 mm
  7. filtrationthen filtered
  8. customto give a beige solid

Sources & evidence

ORD record
ord-88e98d1462714e8cb54d5d2150daed46
Source dataset
uspto-grants-2014_11
Patent number
US08895545B2

Reaction notes

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