Morpholine → HCID 46178248, compound

HRID 220177Notes

Reaction equation

HRID 220177 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=[O:39])/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([C:29](=[O:38])[NH:30][C:31]2[CH:36]=[CH:35][C:34]([Br:37])=[CH:33][CH:32]=2)[CH2:25][CH2:26][CH2:27]Cl)=[CH:20][CH:19]=1)(C)(C)C.[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.Cl.CO.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:37][C:34]1[CH:35]=[CH:36][C:31]([NH:30][C:29](=[O:38])[CH:24]([C:21]2[CH:22]=[CH:23][C:18](/[CH:17]=[CH:16]/[C:15](=[O:39])[NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[NH2:7])=[CH:19][CH:20]=2)[CH2:25][CH2:26][CH2:27][N:41]2[CH2:46][CH2:45][O:44][CH2:43][CH2:42]2)=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 21893726Hydrochloride methanolHCID 59238311HCID 59238311, compound

Product 1

HCID 46178248HCID 46178248, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)-[2-(3-{4-[1-(4-bromo-phenylcarbamoyl)-4-chloro-butyl]-phenyl}-acryloylamino)-phenyl]-carbamic acid tert-butyl ester (187.5 mg, 0.3 mmol) in DMF (3 mL), morpholine (261 mg, 3 mmol) was added. Then the solution was stirred at 80 degrees Celsius overnight. A solution of 1.25 M HCl/MeOH (4 mL) was added to the residue, the solution was stirred for 4 h at ambient temperature. After reaction, the solution was neutralized with solid NaHCO3. The final product was obtained by preparative HPLC. MS: calc'd 577 (MH+), exp 577 (MH+). 1H NMR (d6-DMSO, 400 MHz), 10.33 (s, 1H), 9.57 (broad s, 2H), 7.61 (d, 1H, J=15.6 Hz), 7.59-7.54 (m, 4H), 7.49-7.46 (m, 4H), 7.36 (d, 1H, J=7.6 Hz), 6.99 (t, 1H, J=7.6 Hz), 6.91-6.84 (m, 2H), 6.71 (broad s, 1H), 3.96 (d, 2H, J=12.0 Hz,), 3.75 (t, 1H, J=7.2 Hz,), 3.62 (t, 2H, J=12.0 Hz), 3.40 (broad s, 2H), 3.14 (t, 2H, J=7.6 Hz), 3.03 (broad s, 2H), 2.09-2.04 (m, 1H), 1.78-1.71 (m, 1H), 1.67-1.57 (m, 2H).

Workup

  1. stirringthe solution was stirred for 4 h at ambient temperature
  2. customAfter reaction

Sources & evidence

ORD record
ord-13118d918ea14f8a9c348a21d7115cac
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Reaction notes

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