1,2-Dichloroethane → HCID 22593808, compound

HRID 1761112Notes

Reaction equation

HRID 1761112 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][NH:18][CH2:19][C:20]1[S:24][C:23]2[CH:25]=[CH:26][S:27][C:22]=2[CH:21]=1.C1C=CC2N(O)N=NC=2C=1.O.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:18]([CH3:17])[CH2:19][C:20]2[S:24][C:23]3[CH:25]=[CH:26][S:27][C:22]=3[CH:21]=2)=[O:16])=[CH:8][CH:7]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 10487224(2E)-3-(6-aminopyridin-3-yl)prop-2-enoic acidHCID 22593742HCID 22593742, compound

Product 1

HCID 22593808HCID 22593808, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

EDC (230 mg, 1.2 mmole) was added to a solution (E)-3-(6-aminopyridin-3-yl)acrylic acid (164 mg, 1.0 mmole), 2-(methylaminomethyl)thieno[3,2-b]thiophene (220 mg, 1.2 mmole), HOBt H2O (162 mg, 1.2 mmole), and Et3N (0.35 mL, 2.5 mmole) in dry DMF (5 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 solid was taken up in 1:I MeOH/H2O and filtered. The filtrate was concentrated to approximately ⅓ volume. The precipitate was collected by filtration, washed with H2O, and died in vacuo to afford the title compound (139 mg, 42%) as a light tan solid: 1H NMR (400 MHz, d6-DMSO) δ 8.15 (d, J=2.0 Hz,1H), 7.83 (bd,1H), 7.61 (d, i=5.2 Hz, 1H), 7.40 (m, 3H), 6.45 (m, 2H), 4.75 (s, 2H), 3.13 (s, 3H); for minor rotomer δ5.00 (s, 2H), 2.95 (s, 3H); MS (ES) nm/e 330 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated
  4. filtrationI MeOH/H2O and filtered
  5. concentrationThe filtrate was concentrated to approximately ⅓ volume
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with H2O

Sources & evidence

ORD record
ord-9114f3fbf9e64e479ea522b82f6cd23e
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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