1,2-Dichloroethane → HCID 22593808, compound

HRID 1921046Notes

Reaction equation

HRID 1921046 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.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 757711-HydroxybenzotriazoleHCID 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 962WaterSolvent2×HCID 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 1:1 MeOH/H2O and filtered. The filtrate was concentrated to approximately ⅓ volume. The precipitate was collected by filtration, washed with H2O, and dried 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, J=5.2 Hz, 1H), 7.40 (m, 3H); 6.45 (m, 2H), 4.75 (s, 2H), 3.13 (s, 3H); for minor rotomer δ 5.00 (s, 2H), 2.95 (s, 3H); MS (ES) m/e 330 (M+H)+.

Workup

  1. customat RT
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to approximately ⅓ volume
  7. filtrationThe precipitate was collected by filtration
  8. washwashed with H2O
  9. customdried in vacuo

Sources & evidence

ORD record
ord-8f06f70a7c374befa451c476859a731f
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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