1,2-Dichloroethane → HCID 24891560, compound

HRID 1880003Notes

Reaction equation

HRID 1880003 reaction equation
C(Cl)CCl.[CH3:5][NH:6][CH2:7][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.C[C:20]1([CH3:37])[CH2:26][O:25][C:24]2[CH:27]=[C:28](/[CH:31]=[CH:32]/[C:33]([OH:35])=O)[CH:29]=[N:30][C:23]=2[NH:22][C:21]1=[O:36].C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:37][C:20]1([CH3:26])[O:25][C:24]2[CH:27]=[C:28](/[CH:31]=[CH:32]/[C:33]([N:6]([CH3:5])[CH2:7][C:8]3[NH:9][C:10]4[C:15]([C:16]=3[CH3:17])=[CH:14][CH:13]=[CH:12][CH:11]=4)=[O:35])[CH:29]=[N:30][C:23]=2[NH:22][C:21]1=[O:36]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 26722512N-Methyl-1-(3-methyl-1H-indol-2-YL)methanamineHCID 68410443HCID 68410443, compound

Product 1

HCID 24891560HCID 24891560, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (402 mg, 1.0 mmol) was added to a solution of N-methyl(3-methyl-1H-indol-2-yl)methanamine (135 mg, 0.7 mmol), (E)-3-(3,3-dimethyl-4-oxo-2,3,4,5-tetrahydropyrido[3,2-b][1,4]oxazepin-8-yl)acrylic acid hydrochloride (240 mg, 0.8 mmol), HOBT.H2O (101 mg, 0.7 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 (234 mg, 79%). 1H NMR (300 MHz, DMSO-d6) δ 10.62-10.58 (rotamers, s, 1H), 10.09 (s, 1H), 8.26 (s, 1H), 7.89 (s, 1H), 7.51-7.49 (m, 2H), 7.28 (t, J=8.0 Hz, 1H), 7.03-6.90 (m, 3H), 4.90-4.73 (rotamers, s, 2H), 4.05 (s, 3H), 2.23 (s, 3H), 1.17 (s, 6H); MS (ESI): m/e 419.4 (C24H26N4O3+H)+

Workup

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

Sources & evidence

ORD record
ord-f9ff2e226e4749d0b166e4c02aa3e4f4
Source dataset
uspto-grants-2012_11
Patent number
US08318720B2

Reaction notes

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