4-Methylmorpholine → HCID 86698907, compound

HRID 2179473Notes

Reaction equation

HRID 2179473 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:5]([CH3:14])[N:4]2[C:15]([C:18]([OH:21])([CH3:20])[CH3:19])=[CH:16][N:17]=[C:3]12.[O:22]=[C:23]1[NH:31][C:26]2[N:27]=[CH:28][N:29]=[CH:30][C:25]=2[C@@:24]21[CH2:42][C:34]1=[N:35][CH:36]=[C:37]([C:39](O)=[O:40])[CH:38]=[C:33]1[CH2:32]2.ON1C2N=CC=CC=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.O>[OH:21][C:18]([C:15]1[N:4]2[C@H:5]([CH3:14])[C@H:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:7][C@H:2]([NH:1][C:39]([C:37]3[CH:38]=[C:33]4[CH2:32][C@@:24]5([C:25]6[CH:30]=[N:29][CH:28]=[N:27][C:26]=6[NH:31][C:23]5=[O:22])[CH2:42][C:34]4=[N:35][CH:36]=3)=[O:40])[C:3]2=[N:17][CH:16]=1)([CH3:20])[CH3:19]

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68746693HCID 68746693, compoundHCID 86698908HCID 86698908, compound

Product 1

HCID 86698907HCID 86698907, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(5R,6S,8S)-8-amino-5-methyl-6-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridin-3-yl]propan-2-ol (6.7 mg, 0.023 mmol) in N,N-dimethylformamide (195 μL) was added (6S)-6′-oxo-5,6′,7,7′-tetrahydrospiro[cyclopenta[b]pyridine-6,5′-pyrrolo[2,3-d]pyrimidine]-3-carboxylic acid (5.5 mg, 0.019 mmol), 1-hydroxy-7-azabenzotriazole (0.2 mg, 0.002 mmol), N-methylmorpholine (10.7 μL, 0.097 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.5 mg, 0.023 mmol). The mixture was stirred 2 h. Water was added, and the mixture was purified by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid) giving the title compound (1.4 mg). HRMS 550.2546 (M+1). NMR (500 MHz, CD3OD): δ 8.95 (s, 1H); 8.70 (s, 1H); 8.22 (s, 1H); 8.15 (s, 1H); 7.41−7.27 (m, 5H); 6.86 (s, 1H); 5.43 (dd, J=10.7, 7.5 Hz, 1H); 5.04 (dd, J=7.0, 4.8 Hz, 1H); 3.70−3.41 (m, 5H); 2.70−2.67 (m, 1H); 2.52−2.49 (m, 1H); 1.64 (d, J=13.6 Hz, 6H); 1.32 (d, J=6.4 Hz, 3H).

Workup

  1. customthe mixture was purified by reverse phase chromatography (C-18, 85% water/acetonitrile→5% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d0bafa6d93b7428886557568da2080b4
Source dataset
uspto-grants-2015_06
Patent number
US09067941B2

Reaction notes

Loading…