1,2-Dichloroethane → HCID 178482574, compound

HRID 1921047Notes

Reaction equation

HRID 1921047 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.[CH3:19][N:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=[C:21]1[CH2:29][NH:30][CH3:31].C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>CN(C=O)C.O>[N:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11](/[CH:14]=[CH:15]/[C:16]([N:30]([CH3:31])[CH2:29][C:21]3[N:20]([CH3:19])[C:28]4[C:23]([CH:22]=3)=[CH:24][CH:25]=[CH:26][CH:27]=4)=[O:18])[CH:12]=2)[NH:7][CH:6]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 178525340HCID 178525340, compound

Product 1

HCID 178482574HCID 178482574, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (230 mg, 1.2 mmole) was added to a solution (E)-3-(3H-imidazo[4,5-b]pyridin-6-yl)acrylic acid (189 mg, 1.0 mmole), 1-methyl-2-(methylaminomethyl)-1H-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) δ 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 δ 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. customat RT
  2. filtrationThe title compound (193 mg, 56%) was collected as a white solid by filtration
  3. washwashed with H2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-0d4fcf906fbd4d4799fe1f032c6680bc
Source dataset
uspto-grants-2012_05
Patent number
US08173646B2

Reaction notes

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