1,2-Dichloroethane → HCID 66966361, compound

HRID 1362244Notes

Reaction equation

HRID 1362244 reaction equation
C(Cl)C[Cl:3].[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([OH:16])=O)=[CH:8][CH:7]=1.[CH3:17][NH:18][CH2:19][C:20]1[O:21][C:22]2[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=2[C:24]=1[CH3:25].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl>CN(C=O)C.O.C(Cl)Cl>[ClH:3].[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:18]([CH3:17])[CH2:19][C:20]2[O:21][C:22]3[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=3[C:24]=2[CH3:25])=[O:16])=[CH:8][CH:7]=1

Participants

10

Reactant 6

HCID 111,2-DichloroethaneHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 46785639N-methyl-1-(3-methylbenzofuran-2-yl)methanamine

Product 1

HCID 66966361HCID 66966361, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

EDC (231 mg, 1.2 mmol) was added to a solution of (E)-3-(6-amino-pyridin-3-yl)acrylic acid (164 mg, 1.0 mmol), methyl-(3-methyl-benzofuran-2-ylmethyl)amine (193 mg, 1.1 mmol), HOBt.H2O (149 mg, 1.1 mmol) and DIPEA (525 μL, 3.0 mmol) in dry DMF (10 mL). After 18 hr of stirring, the mixture was diluted with water (60 mL) and extracted with EtOAc (2×20 mL). The oraganic layer was washed with brine (2×30 mL), dried and evaporated. Flash chromatography (silica 1-3% MeOH in CH2Cl2) of the residue furnished pure free base which was dissolved in CH2Cl2 (10 mL). After addition of HCl (1.5 mL, 1M in ether), the solvents were evaporated, washed with ether and dried to afford the title compound (195 mg, 54%). 1H NMR (300 MHz, DMSO-d6) δ 8.36 (m, 3H), 7.50 (m, 3H), 7.25 (m, 3H), 7.02 (m, 1H), 4.98 and 4.79 (rotamers, 2s, 2H), 3.17 and 2.92 (rotamers, 2s, 3H), 2.26 (s, 3H). MS (ESI) m/e 322 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe oraganic layer was washed with brine (2×30 mL)
  3. customdried
  4. customevaporated
  5. customFlash chromatography (silica 1-3% MeOH in CH2Cl2) of the residue furnished pure free base which
  6. customthe solvents were evaporated
  7. washwashed with ether
  8. customdried

Sources & evidence

ORD record
ord-c20224838fa14aa3a7f6a9bf34c90ebb
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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