Methyl 4-Amino-2-chlorobenzoate → HCID 66789084, compound

HRID 1360235Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][CH2:20][N:19]([S:23]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=4[O:33][CH3:34])(=[O:25])=[O:24])[C:18]=3[CH:35]=2)=[O:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:36]OC(=O)C1C=CC(N)=CC=1Cl>>[CH3:36][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([NH:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:22][CH2:21][CH2:20][N:19]([S:23]([C:26]4[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=4[O:33][CH3:34])(=[O:24])=[O:25])[C:18]=3[CH:35]=2)=[O:13])=[CH:10][C:2]=1[Cl:1]

Participants

Reactant 2

HCID 11839197Methyl 4-Amino-2-chlorobenzoate

HCID 24762393HCID 24762393, compound

Product 1

HCID 66789084HCID 66789084, compound

Procedure

2-Chloro-4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-benzoic acid, MS (ISP): m/e=534.9, 536.9 (M−H), was prepared as described in example 1, steps 1 to 6. Step 5 was performed using 4-amino-2-chloro-benzoic acid methyl ester and yielded 2-chloro-4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo-[1,4]oxazine-6-carbonyl]-amino}-benzoic acid methyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record: ord-3412d6ab56d541d7a02998d9177ddb90
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07879845B2

Reaction notes

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