Methyl 4-Formylbenzoate → Methyl 4-([[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate

HRID 630365Notes

Reaction equation

HRID 630365 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:30]=[CH:29][C:16]([O:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[CH:31]([C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[N:23]1([CH2:22][CH2:21][N:20]([CH2:31][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)[CH2:19][CH2:18][O:17][C:16]2[CH:15]=[CH:14][C:13]([CH2:12][C:9]3[CH:10]=[CH:11][C:6]([C:2]4[O:1][CH:5]=[CH:4][N:3]=4)=[CH:7][CH:8]=3)=[CH:30][CH:29]=2)[CH2:24][CH2:25][O:26][CH2:27][CH2:28]1

Participants

6

Reactant 3

HCID 15294Methyl 4-FormylbenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 68488020N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamine

Product 1

HCID 68484695Methyl 4-([[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoateYield 84%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A solution of N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine (0.25 g, 0.6 mmol) and methyl 4-formylbenzoate (0.11 g, 0.66 mmol) in dichloroethane (5 mL) was stirred as sodium triacetoxyborohydride (0.16 g, 0.74 mmol) was added and stirred for 17 h. The reaction was diluted with water and extracted with ethyl acetate. The combined organic extracts were dried and concentrated. Purification by chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.28 g of methyl 4-[[[2-(4-morpholinyl)ethyl][2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]amino]-methyl]benzoate; 1H NMR (400 MHz, CDCl3) δ 7.97 (m, 4H), 7.68 (s, 1H), 7.42 (d, 2H), 7.27 (d, 2H), 7.21 (s, 1H), 7.08 (d, 2H), 6.78 (d, 2H), 4.03 (t, 2H), 3.96 (s, 2H), 3.92 (s, 3H), 3.79 (s, 2H), 3.66 (m, 4H), 2.92 (t, 2H), 2.73 (t, 2H), 2.47 (m, 2H) 2.42 (m, 4H) ppm.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

Sources & evidence

ORD record
ord-33685eee3b404714bcba8f11c6719f26
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

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