1,2-Dichloroethane → HCID 6539893, compound

HRID 225915Notes

Reaction equation

HRID 225915 reaction equation
C(Cl)CCl.[N:5]1[C:14]2[NH:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7](/[CH:15]=[CH:16]/[C:17]([OH:19])=O)[CH:6]=1.[CH3:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]1[CH2:30][NH:31][CH3:32].C1C=CC2N(O)N=NC=2C=1.O.CCN(CC)CC>CN(C=O)C>[CH3:32][N:31]([CH2:30][C:22]1[N:21]([CH3:20])[C:29]2[C:24]([CH:23]=1)=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17](=[O:19])/[CH:16]=[CH:15]/[C:7]1[CH:6]=[N:5][C:14]2[NH:13][CH2:12][CH2:11][CH2:10][C:9]=2[CH:8]=1

Participants

8

Reactant 6

HCID 111,2-DichloroethaneHCID 962WaterHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 11401058methyl((1-methyl-1H-indol-2-yl)methyl)amineHCID 11805816HCID 11805816, compound

Product 1

HCID 6539893HCID 6539893, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

EDC (203 mg, 1.06 mmole) was added to a solution (E)-3-(5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylic acid (180 mg, 0.88 mmole), 1-methyl-2-(methylaminomethyl)-1H-indole (185 mg, 1.06 mmole), HOBt.H2O (143 mg, 1.06 mmole), and Et3N (0.31 mL, 2.2 mmole) in dry DMF (5 mL) at RT. After 18 hr the mixture was concentrated. Flash chromatography on silica gel (10% EtOH/EtOAc) gave the title compound (222 mg, 70%) as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 7.99-6.82 (m, 8 H), 6.40 (s, 1 H), 4.82 (s, 2 H), 3.67 (m, 2 H), 3.29 (m, 3 H), 3.07 (m, 3 H), 2.73 (m, 2 H), 1.77 (m, 2 H); for minor rotomer δ 6.16 (s, 1 H), 5.00 (s, 2 H); MS (ES) m/e 361 (M+H)+.

Workup

  1. customat RT
  2. concentrationAfter 18 hr the mixture was concentrated

Sources & evidence

ORD record
ord-93237afd23324845af0ec3ed7cf80c99
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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