Morpholine → HCID 22022387, compound

HRID 352158Notes

Reaction equation

HRID 352158 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:22][C:21]([C:23]([OH:25])=O)=[CH:20][N:19]=3)=[O:17])=[CH:8]2)=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]([C:18]3[NH:22][C:21]([C:23]([N:40]4[CH2:45][CH2:44][O:43][CH2:42][CH2:41]4)=[O:25])=[CH:20][N:19]=3)=[O:17])=[CH:8]2)=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22022401HCID 22022401, compound

Product 1

HCID 22022387HCID 22022387, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-[1-(4-chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazole-4-carboxylic acid (10 mg, 0.026 mmol), 4-(dimethylamino)pyridine (DMAP) (30 mg, 0.25 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) (30 mg, 0.16 mmol) in CH2Cl2 (2 mL) was stirred at room temperature under N2 for 1 hour. Then morpholine (0.1 mL) in CH2Cl2 (2 mL) was added followed by stirring overnight at room temperature. After removal of solvent, product {2-[1-(4-Chloro-benzyl)-1H-indole-3-carbonyl]-3H-imidazol-4-yl}-morpholin-4-yl-methanone (8 mg, yield 68%) was purified by column chromatography (ethyl acetate:methanol=10:1). 1H NMR (CD3OD) δ3.7 (m, 8H), 5.58 (s, 2H), 7.3-7.45 (m, 7H), 7.80 (s, 1H), 8.42 (m, 1H), 9.05 (s, 1H) ppm; ESMS calcd (C24H21ClN4O3): 448.13; found: 449.1 (M+H)+.

Workup

  1. stirringby stirring overnight at room temperature

Sources & evidence

ORD record
ord-98957f57d431458f9ecefe073a971639
Source dataset
uspto-grants-2004_06
Patent number
US06743919B2

Reaction notes

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