3,4-diamino-N-quinolin-2-yl-benzamide → {3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester

HRID 1515018Notes

Reaction equation

HRID 1515018 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[NH2:21])[C:5]([NH:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=1)=[O:6].[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:32]=[C:31]([Cl:33])[C:30]([CH:34]=O)=[C:29]([Cl:36])[CH:28]=1>>[CH3:22][O:23][C:24](=[O:37])[CH2:25][O:26][C:27]1[CH:28]=[C:29]([Cl:36])[C:30]([C:34]2[NH:1][C:2]3[CH:3]=[C:4]([C:5](=[O:6])[NH:7][C:8]4[CH:17]=[CH:16][C:15]5[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=5)[N:9]=4)[CH:18]=[CH:19][C:20]=3[N:21]=2)=[C:31]([Cl:33])[CH:32]=1

Participants

3

Reactant 2

HCID 669657403,4-diamino-N-quinolin-2-yl-benzamideHCID 85876215HCID 85876215, compound

Product 1

HCID 66965705{3,5-Dichloro-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenoxy}-acetic acid methyl ester

Procedure

The title compound was prepared from 3,4-diamino-N-quinolin-2-yl-benzamide (from Example 6-17) and (3,5-dichloro-4-formylphenoxy)-acetic acid methyl ester (from Example 6-5) analogous to Example 6-17. 1H NMR (Methanol-d4, 400 MHz): δ 8.44 (m, 3H), 8.06 (d, 1H), 7.92 (d, 2H), 7.74 (m, 2H), 7.54 (m, 1H), 7.23 (s, 2H), 4.89 (s, 2H), 3.82 (s, 3H). MS (m/z) 521.2 (M+1); Retention time: 1.42 min (Method 10).

Sources & evidence

ORD record
ord-4f694fd733ac4058a5563db647d4e05e
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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