4-Methylmorpholine → HCID 86591639, compound

HRID 2415128Notes

Reaction equation

HRID 2415128 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][CH2:16][CH2:17][CH2:18][NH2:19])[CH:6]=1.[CH2:20]([N:27]1[C:35]2[C:30](=[C:31]([Cl:37])[CH:32]=[C:33]([Cl:36])[CH:34]=2)[CH:29]=[C:28]1[C:38](O)=[O:39])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]=[C:7]([NH:15][CH2:16][CH2:17][CH2:18][NH:19][C:38]([C:28]2[N:27]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:35]3[C:30]([CH:29]=2)=[C:31]([Cl:37])[CH:32]=[C:33]([Cl:36])[CH:34]=3)=[O:39])[CH:6]=1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22640710HCID 22640710, compoundHCID 22640745HCID 22640745, compound

Product 1

HCID 86591639HCID 86591639, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N1-(4-methoxyquinolin-2-yl)propane-1,3-diamine dihydrochloride (193 mg, 0.63 mmol) [from example 1d], 1-benzyl4,6-dichloro-1H-indole-2-carboxylic acid (203 mg, 0.63 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (182 mg, 0.95 mmol), 1-hydroxybenzotriazole hydrate (94 mg, 0.70 mmol), and N-methylmorpholine (244 μl, 2.22 mmol) in anhydrous N,N-dimethylformamide (5 ml) was stirred for 2 days. The resulting slurry was taken into water (50 ml) and 10% sodium hydroxide solution (10 ml). Extracted into ethyl acetate. The extracts were dried (sodium sulfate) and evaporated to an oil. Column chromatography on silica (2:1 ethyl acetate/hexanes) gave 1-benzyl-4,6-dichloro-1H-indole-2-carboxylic acid [3-(4-methoxy-quinolin-2-ylamino)-propyl]-amide (269 mg, 80%) as a white solid. [M+H]+ 533.

Workup

  1. extractionExtracted into ethyl acetate
  2. dry with materialThe extracts were dried (sodium sulfate)
  3. customevaporated to an oil

Sources & evidence

ORD record
ord-f20d9b2b02374eba88855dc5936e9a2d
Source dataset
uspto-grants-2004_11
Patent number
US06818655B2

Reaction notes

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