1,2-Dichloroethane → HCID 178482574, compound

HRID 1761113Notes

Reaction equation

HRID 1761113 reaction equation
C(Cl)CCl.[N:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11](/[CH:14]=[CH:15]/[C:16]([OH:18])=O)[CH:12]=2)[NH:7][CH:6]=1.[CH:19]1[CH:20]=[CH:21][C:22]2N(O)N=N[C:23]=2[CH:24]=1.O.C[CH2:31][N:32](CC)[CH2:33]C.[CH3:37][N:38]([CH:40]=O)[CH3:39]>O>[N:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11](/[CH:14]=[CH:15]/[C:16]([N:32]([CH3:33])[CH2:31][C:37]3[N:38]([CH3:39])[C:40]4[C:19]([CH:24]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[O:18])[CH:12]=2)[NH:7][CH:6]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 178525340HCID 178525340, compound

Product 1

HCID 178482574HCID 178482574, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

EDC (230 mg, 1.2 mmole) was added to a solution (E)3-(3H-imidazo[4,5-b]pyridin-6yl)acrylic acid (189 mg, 1.0 mmole), 1-methyl-2-(methylaminomethyl)-11H-indole (209 mg, 1.2 mmole), HOBt H2O (162 mg, 1.2 mmole), and Et3N (0.28 mL, 2.0 mmole) in dry DMF (5 mL) at RT. After 18 hr the mixture was diluted with H2O. The title compound (193 mg, 56%) was collected as a white solid by filtration, washed with H2O, and dried in vacuo: 1H NMR (400 MHz, d6-DMSO) & 8.72 (s,1H), 8.50 (s, 2H), 7.68 (d,J=15.4 Hz,1H), 7.45 (m, 3H), 7.13 (m,1H), 7.01 (m,1H), 6.43 (s,1H), 4.87 (s, 2H), 3.70 (s, 3H), 3.15 (s, 3H); for minor rotomer 5 8.68 (s,1H). 8.47 (s, 2H), 6.19 (s, 1H), 5.10 (s, 2H), 3.74 (s, 3H), 3.01 (s, 3H); MS (ES) m/e 346 (M+H)+.

Workup

  1. filtrationThe title compound (193 mg, 56%) was collected as a white solid by filtration
  2. washwashed with H2O
  3. customdried in vacuo

Sources & evidence

ORD record
ord-219da9949c5d4d0b93003b2028eed2d0
Source dataset
uspto-grants-2005_01
Patent number
US06846819B1

Reaction notes

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