N,N-Dimethylglycine → HCID 66621381, compound

HRID 415322Notes

Reaction equation

HRID 415322 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][C:4](O)=[O:5].Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH:39]1[CH2:44][CH2:43][CH2:42][CH:41]([C:45]2[CH:50]=[CH:49][C:48]([C:51]3[O:52][C:53]4[C:59]([C:60]([NH2:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:54]=4[N:55]=3)=[CH:47][CH:46]=2)[CH2:40]1>CN(C=O)C.O.C(OCC)(=O)C>[CH3:1][N:2]([CH3:7])[CH2:3][C:4]([N:39]1[CH2:44][CH2:43][CH2:42][CH:41]([C:45]2[CH:50]=[CH:49][C:48]([C:51]3[O:52][C:53]4[C:59]([C:60]([NH2:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:54]=4[N:55]=3)=[CH:47][CH:46]=2)[CH2:40]1)=[O:5]

Participants

9

Reactant 5

HCID 673N,N-DimethylglycineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 44181679HCID 44181679, compound

Product 1

HCID 66621381HCID 66621381, compoundYield 15.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(dimethylamino)acetic acid (648 mg, 2.02 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (186 mg, 0.97 mmol), 1-hydroxybenzotriazole (131 mg, 0.97 mmol) in N,N′-dimethylformamide (50 ml) was added diisopropylethylamine (280 mg). The mixture was stirred at room temperature for 0.5 h. 2-(4-(Piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (260 mg, 0.81 mmol) was added to the reaction mixture at 0° C. Then the mixture was stirred at room temperature for 4 h. Then ethyl acetate and water was added to the mixture and extracted. The organic phase was washed with water (50 mL×3), brine (50 mL), dried over anhydrous sodium sulfate, and concentrated to give crude product which was purified by chromatography (silica gel, dichloromethane/methanol=10:1) to give 2-(4-(1-(2-(dimethylamino)acetyl)piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (50 mg, Yield: 15%). 1H-NMR (400 MHz, DMSO-d6) δ: 1.41-1.58 (m, 1H), 1.76-1.84 (m, 2H), 1.96-1.98 (m, 1H), 2.10 (s, 6H), 2.54-2.88 (m, 2H), 2.93-3.09 (m, 2H), 3.14-3.26 (m, 2H), 4.11 (t, J=12 Hz, 1H), 4.44 (t, J=9.2 Hz, 1H), 7.48 (t, J=8.0 Hz, 1H), 7.54-7.57 (dd, J1=8.0 Hz, J2=2.4 Hz, 2H), 7.81 (d, J=8.0 Hz, 1H), 7.87 (brs, 1H), 7.90 (brs, 1H), 7.95 (d, J=7.6 Hz, 1H), 8.24-8.26 (dd, J1=8.0 Hz, J2=5.6 Hz, 2H); LC-MS (ESI) m/z: 407 (M+1)+.

Workup

  1. stirringThen the mixture was stirred at room temperature for 4 h
  2. extractionextracted
  3. washThe organic phase was washed with water (50 mL×3), brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product which
  7. customwas purified by chromatography (silica gel, dichloromethane/methanol=10:1)

Sources & evidence

ORD record
ord-33a5fb5b263f42c19593e5ef03f8c352
Source dataset
uspto-grants-2012_01
Patent number
US08088760B2

Reaction notes

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