1,2-Dichloroethane → HCID 86606147, compound

HRID 1362424Notes

Reaction equation

HRID 1362424 reaction equation
C(Cl)CCl.CNC[C:8]1[NH:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=2.Cl.[NH2:19][C:20]1[N:25]=[CH:24][C:23](/[CH:26]=[CH:27]/C(O)=O)=[CH:22][CH:21]=1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:50][N:51]([CH:53]=[O:54])[CH3:52]>O>[NH2:19][C:20]1[N:25]=[CH:24][C:23]([C:26](=[CH2:27])[C:53]([N:51]([CH3:52])[CH2:50][C:8]2[NH:9][C:10]3[C:15]([C:16]=2[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:54])=[CH:22][CH:21]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 26722512N-Methyl-1-(3-methyl-1H-indol-2-YL)methanamineHCID 66967187(E)-3-(6-aminopyrid-3-yl)acrylic acid hydrochloride

Product 1

HCID 86606147HCID 86606147, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

EDC (438 mg, 1.1 mmol) was added to a solution of N-methyl-(3-methyl-1H-indol-2-yl)methanamine (170 mg, 0.9 mmol), (E)-3-(6-aminopyrid-3-yl)acrylic acid hydrochloride (176 mg, 1.0 mmol), HOBT.H2O (130 mg, 0.9 mmol) and DIPEA (0.58 mL, 2.7 mmol) in dry DMF (5 mL). After stirring overnight, water was added. The precipitate that formed was washed with ethyl acetate and dried to afford the title compound (65 mg, 23%). 1H NMR (300 MHz, DMSO-d6) δ 10.75-0.54 (rotamers, s, 1H), 8.15 (d, J=7.2 Hz, 1H), 7.94 (s, 1H), 7.84 (d, J=7.7 Hz, 1H), 7.40 (d, J=7.0 Hz, 1H), 7.31 (d, J=7.9 Hz, 1H), 7.02-6.97 (m, 2H), 6.47-6.41 (m, 2H), 5.01-4.85 (rotamers, s, 2H), 4.72 (s, 3H), 2.23 (s, 3H); MS (ESI): m/e 321.3 (C19H20N4O+H)+.

Workup

  1. customThe precipitate that formed
  2. washwas washed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-5095817f41b346bc8b20a00fd7846c98
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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