(4-chloro-2-Methylphenoxy)acetic acid → 5-[4-[2-(4-Chloro-2-methylphenoxy)acetylamino]phenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

HRID 1049747Notes

Reaction equation

HRID 1049747 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([OH:10])=O)=[C:4]([CH3:13])[CH:3]=1.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[C:27](=[O:28])[CH2:26][C:25](=[O:29])[NH:24][C:23]3[C:30]4[C:35]([CH:36]=[CH:37][C:22]2=3)=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:17][CH:16]=1.ClC1C=CC(OCC(Cl)=O)=C(C)C=1>>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][C:8]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[C:27](=[O:28])[CH2:26][C:25](=[O:29])[NH:24][C:23]4[C:30]5[C:35]([CH:36]=[CH:37][C:22]3=4)=[CH:34][CH:33]=[CH:32][CH:31]=5)=[CH:17][CH:16]=2)=[O:10])=[C:4]([CH3:13])[CH:3]=1

Participants

4

Reactant 3

HCID 7204(4-chloro-2-Methylphenoxy)acetic acidHCID 12353489(2-Methyl-4-chlorophenoxy)acetyl chlorideHCID 1176991675-(4-Aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione

Product 1

HCID 1176995695-[4-[2-(4-Chloro-2-methylphenoxy)acetylamino]phenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dioneYield 99%

Procedure

(4-Chloro-2-methylphenoxy)acetic acid (38 mg, 0.189 mmol) was made into acid chloride in a conventional manner. By using 5-(4-aminophenyl)-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (30 mg, 0.095 mmol) obtained in Example 1, and (4-chloro-2-methylphenoxy)acetic acid chloride mentioned above, the title compound (47 mg, yield 99%) was obtained in the same manner as that of Example 1.

Sources & evidence

ORD record
ord-6789c530195345dfa7e18d11a46d50bf
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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