1,2-Dichloroethane → HCID 22593721, compound

HRID 225919Notes

Reaction equation

HRID 225919 reaction equation
C(Cl)CCl.[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][N:18]1[C:22]([CH2:23][NH:24][CH3:25])=[CH:21][C:20]2[CH:26]=[CH:27][S:28][C:19]1=2.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[NH2:5][C:6]1[N:11]=[CH:10][C:9](/[CH:12]=[CH:13]/[C:14]([N:24]([CH3:25])[CH2:23][C:22]2[N:18]([CH3:17])[C:19]3[S:28][CH:27]=[CH:26][C:20]=3[CH:21]=2)=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 22593772HCID 22593772, compound

Product 1

HCID 22593721HCID 22593721, compoundYield 34.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (132 mg, 0.69 mmole) was added to a solution (E)-3-(6-aminopyridin-3-yl)acrylic acid (95 mg, 0.58 mmole), 6-methyl-5-(methylaminomethyl)-6H-thieno[2,3-b]pyrrole (142 mg, 0.69 mmole), HOBt.H2O (93 mg, 0.69 mmole), and Et3N (0.16 mL, 1.16 mmole) in dry DMF (3 mL) at RT. After 18 hr the mixture was diluted with H2O and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated. The residue was taken up in MeOH and collected by filtration to give the title compound (65 mg, 34%) as a yellow solid: 1H NMR (400 MHz, d6-DMSO) δ 8.15 (s, 1 H), 7.81 (d, J=8.1 Hz, 1 H), 7.43 (d, J=15.2 Hz, 1 H), 6.96 (m, 2 H), 6.43 (m, 3 H), 4.70 (s, 2 H), 3.61 (s, 3 H), 3.00 (s, 3 H); for minor rotomer δ 4.87 (s, 2 H), 2.90 (s, 3 H); MS (ES) m/e 327 (M+H)+.

Workup

  1. customat RT
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3237722ac7444403ab57b02aba4ecfca
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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