1,2-Dichloroethane → HCID 16661579, compound

HRID 1362457Notes

Reaction equation

HRID 1362457 reaction equation
C(Cl)CCl.Cl.[O:6]=[C:7]1[NH:16][C:15]2[N:14]=[CH:13][C:12](/[CH:17]=[CH:18]/[C:19]([OH:21])=O)=[CH:11][C:10]=2[CH:9]=[CH:8]1.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>[CH3:32][N: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:19](=[O:21])/[CH:18]=[CH:17]/[C:12]1[CH:13]=[N:14][C:15]2[NH:16][C:7](=[O:6])[CH:8]=[CH:9][C:10]=2[CH:11]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamineHCID 66966635HCID 66966635, compound

Product 1

HCID 16661579HCID 16661579, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

EDC (0.18 g, 0.95 mmol) was added to a suspension of (E)-3-(7-oxo-7,8-dihydro-1,8-naphthyridin-3-yl)acrylic acid hydrochloride (0.20 g, 0.79 mmol), HOBt (0.12 g, 0.87 mmol), Methyl-(3-methyl-benzofuran-2-ylmethyl)-amine (0.15 g, 0.87 mmol) and (i-Pr)2EtN (0.8 mL, 4.74 mmol) in DMF (10 mL). The mixture was heated at 40° C. overnight then diluted with H2O (30 mL) with rapid stirring. The resulting precipitate was filtered, washed with H2O (20 mL) and dried under high vacuum for 4 hours. The solid was suspended in 50% Et2O:hexanes (20 mL), sonicated then filtered and dried under vacuum overnight. Yield: 0.13 g (44.1%) as a mixture of amide rotamers; 1H NMR (300 MHz, DMSO-d6) δ 12.33 (s, 1H), 8.90 and 8.87 (2×s, 1H), 8.53 (s, 1H), 7.91 (d, 1H, J=9 Hz), 7.65-7.25 (m, 6H), 6.63 (d, 1H, J=9.0 Hz), 5.04 and 4.83 (2×s, 2H), 3.23 and 2.96 (2×s, 3H), 2.29 (s, 3H); ESI MS m/z 374 [C22H19N3O3+H]+

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with H2O (20 mL)
  3. customdried under high vacuum for 4 hours
  4. customhexanes (20 mL), sonicated
  5. filtrationthen filtered
  6. customdried under vacuum overnight
  7. additionYield: 0.13 g (44.1%) as a mixture of amide rotamers

Sources & evidence

ORD record
ord-44163a5453c4447b90006756bf60a75c
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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