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1,2-Dichloroethane → (E)-N-((3-ethyl-1H-indol-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide

HRID 1362436
Notes
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Reaction equation

HRID 1362436 reaction equation
C(Cl)CCl.[CH2:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:16][NH:17][CH3:18])[CH3:6].Cl.[O:20]=[C:21]1[NH:30][C:29]2[N:28]=[CH:27][C:26](/[CH:31]=[CH:32]/[C:33]([OH:35])=O)=[CH:25][C:24]=2[CH2:23][CH2:22]1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH2:5]([C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][C:8]=1[CH2:16][N:17]([CH3:18])[C:33](=[O:35])/[CH:32]=[CH:31]/[C:26]1[CH:27]=[N:28][C:29]2[NH:30][C:21](=[O:20])[CH2:22][CH2:23][C:24]=2[CH:25]=1)[CH3:6]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 59277537(3-ethyl-1H-indol-2-yl)-N-methylmethanamineHCID 66905305(E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic Acid Hydrochloride

Product 1

HCID 16661418
(E)-N-((3-ethyl-1H-indol-2-yl)methyl)-N-methyl-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
Yield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (83 mg, 0.4 mmol) was added to a solution of (3-ethyl-1H-indol-2-yl)-N-methylmethanamine (62.7 mg, 0.3 mmol), (E)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-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 (77.8 mg, 67%). 1H NMR (400 MHz, DMSO-d6) δ 10.61-10.59 (rotamers, s, 2H), 8.36 (s, 1H), 8.07 (s, 1H), 7.51-7.46 (m, 3H), 7.30 (d, J=7.8 Hz, 1H), 7.03 (t, J=7.6 Hz, 1H), 6.95 (t, J=7.2 Hz, 1H), 4.94 (s, 2H), 4.90-4.75 (rotamers, s, 3H), 3.29 (m, 2H), 3.08-2.91 (m, 4H), 1.13 (t, J=7.6 Hz, 3H); MS (ESI): m/e 389.2 (C23H24N4O2+H)+.

Workup

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

Sources & evidence

ORD record
ord-41d0ed23aa734f67a482ae3707994752
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879872B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes