Morpholine → HCID 178427390, compound

HRID 74447Notes

Reaction equation

HRID 74447 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:31]([C:34]2[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=2)(=[O:33])=[O:32])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:28]([OH:30])=O)=[CH:23][CH:22]=2)=[O:18].[NH:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1.Cl.CN(C)CCCN=C=NCC>O.O1CCCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:31]([C:34]2[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=2)(=[O:33])=[O:32])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:28]([N:41]1[CH2:46][CH2:45][O:44][CH2:43][CH2:42]1)=[O:30])=[CH:23][CH:22]=2)=[O:18]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178427391HCID 178427391, compound

Product 1

HCID 178427390HCID 178427390, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-[5-Amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazole-4-carbonyl]-1-(toluene-4-sulfonyl)-1H-indole-5-carboxylic acid (113 mg) was dissolved in water (5 ml) and tetrahydrofuran (THF) (10 ml), and then morpholine (53.5 μl) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (WSC-HCl) (43 mg) were added thereto. The mixture was stirred at room temperature for 24 hours. The reaction mixture was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 17/100) to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[5-(morpholine-4-carbonyl)-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (59 mg).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (methanol/dichloromethane=0/100 to 17/100)

Sources & evidence

ORD record
ord-849b9b6015fa4fe9836e9e315ed292fd
Source dataset
uspto-grants-2014_09
Patent number
US08829199B2

Reaction notes

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