Morpholine → HCID 9818564, compound

HRID 1420548Notes

Reaction equation

HRID 1420548 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14]3[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=3[N:12]=[CH:11]2)[CH:7]=[CH:8][CH:9]=1)([OH:3])=O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.[NH:37]1[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1>CN(C)C=O.C(OCC)(=O)C.O>[N:37]1([C:1]([C:4]2[CH:5]=[C:6]([N:10]3[C:14]4[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=4[N:12]=[CH:11]3)[CH:7]=[CH:8][CH:9]=2)=[O:3])[CH2:42][CH2:41][O:40][CH2:39][CH2:38]1

Participants

8

Reactant 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 11139613HCID 11139613, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 9818564HCID 9818564, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(3-carboxyphenyl)-5-methylbenzimidazole (50 mg, 0.19 mM), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide, HCl (76 mg, 0.39 mM), hydroxybenzotriazole (53 mg, 0.39 mM) in dimethylformamide (2 ml) was treated with triethylamine (80 μl, 0.39 mM) and morpholine (20 μl, 0.22 mM) and the reaction stirred for 18 hours at room temperature under N2. Dilution with water and extractive work up with ethyl acetate was followed by chromatography on silica gel. Yield 37 mg. 1H NMR (360 MHz, DMSO) 2.51 (3H, s), 3.47-3.73 (8H, m), 7.16 (1H, d, J=8.3 Hz), 7.41 (1H, d, J=8.3 Hz), 7.45 and 7.47 (1H, dt, J=1.4 Hz, 7.0 Hz), 7.57-7.60 (3H, m), 7.66 (1H, s) and 8.08 (1H, s). MS M+ 322.

Sources & evidence

ORD record
ord-e734c772163a4e098e175d9248cd9529
Source dataset
uspto-grants-2000_06
Patent number
US06071909

Reaction notes

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