1,2-Dichloroethane → HCID 66967111, compound

HRID 2097141

Reaction equation

HRID 2097141 reaction equation
C(Cl)CCl.C[C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[NH:8][C:7]=1[CH2:15]NC.Cl.[O:19]=[C:20]1[NH:29][C:28]2[N:27]=[CH:26][C:25]([CH:30]=[CH:31][C:32]([OH:34])=O)=[CH:24][C:23]=2[CH2:22][CH2:21]1.C1C=CC2N(O)N=[N:41][C:39]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:39][NH:41][C:32](=[O:34])[C:31]([CH2:15][C:7]1[NH:8][C:9]2[C:14]([CH:6]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:30][C:25]1[CH:26]=[N:27][C:28]2[NH:29][C:20](=[O:19])[CH2:21][CH2:22][C:23]=2[CH:24]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 26722512N-Methyl-1-(3-methyl-1H-indol-2-yl)methanamineHCID 669053063-(7-Oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)acrylic acid hydrochloride

Product 1

HCID 66967111HCID 66967111, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

EDC (498 mg, 2.6 mmol) was added to a solution of 3-methyl-2-(methylaminomethyl)indole (348 mg, 2.0 mmol), 3-(7-oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)-acrylic acid hydrochloride (533 mg, 2.1 mmol), HOBT.H2O (270 mg, 2.0 mmol) and DIPEA (1.04 mL, 6 mmol) in DMF (5 mL). After stirring overnight, the mixture was slowly diluted with water (50 mL). The resulting precipitate was collected by filtration washed with water and dried. The precipitate was suspended in MeOH (10 mL), stirred for 60 hours, filtered and dried to afford title compound (203 mg, 27%). 1H NMR (300 MHz, DMSO-d6, 8): 10.77 and 10.58 (rotamers, 2s, br, 1H), 10.64 (s, br, 1H), 8.37 (d, J=1.9 Hz, 1H), 8.08 (s, 1H), 7.58-6.92 (m, 6H), 4.91 and 4.75 (rotamers, 2s, 2H), 3.09 and 2.91 (rotamers, 2s, 3H), 2.90 (m, 2H), 2.53, (m, 2H), 2.25 (s, 3H). MS (ESI): m/e 375 (M+H)+.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water
  3. customdried
  4. stirringstirred for 60 hours
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-e98d33029fdc47fa98c3609c0cc502a0
Source dataset
uspto-grants-2013_05
Patent number
US08450307B2

Linked notes

Loading…