4-Methylmorpholine → HCID 71550887, compound

HRID 2179461Notes

Reaction equation

HRID 2179461 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][N:13]2[C:15]([C:18]([O:21][CH3:22])([CH3:20])[CH3:19])=[CH:16][N:17]=[C:12]2[C@@H:11]([NH2:23])[CH2:10]1.[O:24]=[C:25]1[NH:33][C:28]2=[N:29][CH:30]=[CH:31][CH:32]=[C:27]2[C@@:26]21[CH2:44][C:36]1=[N:37][CH:38]=[C:39]([C:41](O)=[O:42])[CH:40]=[C:35]1[CH2:34]2.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@H:9]1[CH2:14][N:13]2[C:15]([C:18]([O:21][CH3:22])([CH3:19])[CH3:20])=[CH:16][N:17]=[C:12]2[C@@H:11]([NH:23][C:41]([C:39]2[CH:40]=[C:35]3[CH2:34][C@@:26]4([C:27]5[C:28](=[N:29][CH:30]=[CH:31][CH:32]=5)[NH:33][C:25]4=[O:24])[CH2:44][C:36]3=[N:37][CH:38]=2)=[O:42])[CH2:10]1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68746980(S)-2'-oxo-1',2',5,7-tetrahydrospiro(cyclopenta(b)pyridine-6,3'-pyrrolo(2,3-b)-bipyridine)-3-carboxylic acidHCID 86698905HCID 86698905, compound

Product 1

HCID 71550887HCID 71550887, compoundYield 25.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (6S,8S)-6-(2,3-difluorophenyl)-3-(2-methoxypropan-2-yl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-8-amine (11.0 mg, 0.034 mmol) in N,N-dimethylformamide (342 μL) were added (6S)-2′-oxo-1′,2′,5,7-tetrahydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridine]-3-carboxylic acid (10.6 mg, 0.038 mmol), 1-hydroxy-7-azabenzotriazole (0.5 mg, 3.4 μmol), N-methylmorpholine (4.1 μL, 0.038 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (7.2 mg, 0.038 mmol). The mixture was stirred 45 min. Water was added, and the mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) giving the title compound (5 mg). HRMS 585.2403 (M+1). 1H NMR (400 MHz, DMSO): δ 11.12 (s, 1H); 9.08 (d, J=8.5 Hz, 1H); 8.89 (d, J=2.0 Hz, 1H); 8.12 (d, J=1.9 Hz, 1H); 8.09 (dd, J=5.3, 1.6 Hz, 1H); 7.47 (dd, J=7.3, 1.6 Hz, 1H); 7.41−7.38 (m, 1H); 7.33−7.25 (m, 2H); 6.93 (dd, J=7.3, 5.3 Hz, 1H); 6.83 (s, 1H); 5.50−5.43 (m, 1H); 4.48 (dd, J=11.9, 4.0 Hz, 1H); 3.88 (d, J=11.9 Hz, 1H); 3.40 (d, J=16.6 Hz, 2H); 3.31 (m, 2H); 2.98 (s, 3H); 2.67 (q, J=1.9 Hz, 1H); 2.34−2.31 (m, 2H); 1.51−1.43 (m, 6H).

Workup

  1. customthe mixture was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-7f4c280ce8d848b287b3633eacdf9ff9
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

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