1,2-Dichloroethane → HCID 67507904, compound

HRID 1431774Notes

Reaction equation

HRID 1431774 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]=[C:27]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[CH:28]=3)[C:23](O)=[O:24])=[C:7]([CH3:18])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=3)=[N:9]2)=[CH:4][CH:3]=1.C(Cl)CCl.[CH:39]1([NH2:42])[CH2:41][CH2:40]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:39]1([NH:42][C:23](=[O:24])[C:22]2[CH:26]=[C:27]([N:29]3[CH2:30][CH2:31][O:32][CH2:33][CH2:34]3)[CH:28]=[C:20]([NH:19][C:6]3[C:5]4[C:10](=[CH:11][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[C:8]([C:12]4[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=4)[C:7]=3[CH3:18])[CH:21]=2)[CH2:41][CH2:40]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 59631079HCID 59631079, compound

Product 1

HCID 67507904HCID 67507904, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Prepared according to Procedure U by stirring 3-(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-ylamino)-5-morpholinobenzoic acid (0.030 g, 0.065 mmol), DMAP (0.016 g, 0.131 mmol), EDC (0.025 g, 0.131 mmol), cyclopropylamine (6.46 μL, 0.092 mmol), and DCM (0.6 mL) at 23° C. for 1 hour. Purification by reverse-phase HPLC afforded N-cyclopropyl-3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)benzamide as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.71 (1H, m), 8.61 (1H, s), 8.24 (1H, d, J=4.3 Hz), 8.08 (1H, dd, J=9.3, 6.2 Hz), 7.99 (1H, dd, J=7.6, 1.8 Hz), 7.85-7.89 (1H, m), 7.74 (1H, dd, J=10.4, 2.7 Hz), 7.45-7.51 (2H, m), 6.82-6.84 (1H, m), 6.59-6.61 (1H, m), 6.44 (1H, t, J=2.2 Hz), 3.68-3.74 (4H, m), 3.04-3.09 (4H, m), 2.76 (1H, m), 2.18 (3H, s), 0.60-0.69 (2H, m), 0.51 (2H, dd, J=4.2, 2.2 Hz). Mass Spectrum (ESI) m/e=498.0 (M+1).

Workup

  1. customPrepared
  2. customPurification by reverse-phase HPLC

Sources & evidence

ORD record
ord-62f6ddc18cdb43a8b17fcaf5ae6080e2
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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