4-Methylmorpholine → HCID 22601443, compound

HRID 970922Notes

Reaction equation

HRID 970922 reaction equation
CCN=C=NCCCN(C)C.[NH2:12][CH2:13][C:14]1[CH:43]=[CH:42][C:17]([CH2:18][N:19]([CH:32]2[CH2:41][C:40]3[N:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH2:34][CH2:33]2)[S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[Cl:44][C:45]1[CH:53]=[N:52][CH:51]=[C:50]([Cl:54])[C:46]=1[C:47](O)=[O:48].ON1C2C=CC=CC=2N=N1.CN1CCOCC1>>[Cl:44][C:45]1[CH:53]=[N:52][CH:51]=[C:50]([Cl:54])[C:46]=1[C:47]([NH:12][CH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][N:19]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-:31])=[O:30])(=[O:21])=[O:22])[CH:32]2[CH2:41][C:40]3[N:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH2:34][CH2:33]2)=[CH:42][CH:43]=1)=[O:48]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide2×HCID 757711-HydroxybenzotriazoleHCID 6057633,5-Dichloroisonicotinic acidHCID 22601492HCID 22601492, compound

Product 1

HCID 22601443HCID 22601443, compoundYield 40%

Procedure

Using the EDCI coupling general procedure F: Reaction of N-(4-Aminomethyl-benzyl)-2-nitro-N-(5,6,7,8-tetrahydro-quinolin-7-yl)-benzenesulfonamide (75 mg, 0.17 mmol), 3,5-dichloroisonicotinic acid (75%, 55 mg, 0.22 mmol), 1-hydroxybenzotriazole (23 mg, 0.17 mmol), 4-methyl morpholine (100 uL, 0.89 mmol), and EDCI (32 mg, 0.17 mmol) for two days at 50° C. followed by column chromatography on silica gel (1:1:98 MeOH—NH4OH—CH2Cl2) gave the title compound (42 mg, 40%) as a yellow foam.

Sources & evidence

ORD record
ord-39fe73d7764f4e919c01aaf6b7643911
Source dataset
uspto-grants-2007_12
Patent number
US07312234B2

Reaction notes

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