Morpholine → HCID 136176950, compound

HRID 632928Notes

Reaction equation

HRID 632928 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:18][C:19]3[N:28]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])[C:27](=[O:37])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]=4[C:38]#[C:39][CH2:40][CH2:41][CH2:42][C:43](O)=[O:44])[N:20]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:3]=12.CCN=C=NCCCN(C)C.Cl.[NH:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1>CN(C)C1C=CN=CC=1.CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH2:18][C:19]3[N:28]([CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])[C:27](=[O:37])[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]=4[C:38]#[C:39][CH2:40][CH2:41][CH2:42][C:43]([N:58]4[CH2:63][CH2:62][O:61][CH2:60][CH2:59]4)=[O:44])[N:20]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[C:3]=12

Participants

7

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136380632HCID 136380632, compound

Product 1

HCID 136176950HCID 136176950, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 4 (16.0 mg, 26 μmol), 4-dimethylaminopyridine (0.6 mg, 5.2 μmol), and EDC hydrochloride (5.3 mg, 28 μmol) in DMF (0.5 mL) was added morpholine (2.3 μL, 26 μmol). The reaction mixture was stirred at RT overnight and then diluted with water (5.0 mL). The resulting solid was collected by filtration and purified by flash column chromatography, eluting with 0-7% methanol in DCM to afford the title compound, Example 5, (7.0 mg, 57%) as a yellow solid: m/z 689/691 (M+H)+ (ES+); Rt 3.54 min; 1H NMR (500 MHz, DMSO-d6) δ: 1.71 (2H, quin), 2.43-2.49 (2H, m), 2.52-2.55 (2H, m), 3.20-3.26 (2H, m), 3.28-3.33 (4H, m), 3.44 (2H, t), 5.28 (2H, s), 5.72 (2H, s), 6.17 (1H, d), 6.78 (1H, t), 6.87 (2H, d), 7.02 (1H, t), 7.10 (1H, d), 7.32 (2H, d), 7.60 (1H, d), 7.67 (1H, d), 7.79 (1H, t), 8.16 (1H, s), 9.75 (1H, s).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. custompurified by flash column chromatography
  3. washeluting with 0-7% methanol in DCM

Sources & evidence

ORD record
ord-c101de9d226548cf8976f5165a71b0d2
Source dataset
uspto-grants-2016_04
Patent number
US09321773B2

Reaction notes

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