3-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acid → Methyl 2-amino-5-chloro-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate

HRID 1808896Notes

Reaction equation

HRID 1808896 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]([C:14]([OH:16])=O)=[C:12]([CH3:17])[O:11][N:10]=1.[NH2:18][C:19]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[C:26]([Cl:35])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]>>[NH2:18][C:19]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][N:32]([C:14]([C:13]3[C:9]([C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=4[O:2][CH3:1])=[N:10][O:11][C:12]=3[CH3:17])=[O:16])[CH2:31][CH2:30]2)[C:26]([Cl:35])=[CH:25][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

Participants

3

Reactant 2

HCID 64841003-(2-Methoxyphenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 66691661Methyl 2-amino-5-chloro-4-(piperazin-1-yl)benzoate

Product 1

HCID 66691522Methyl 2-amino-5-chloro-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate

Procedure

3-(2-Methoxyphenyl)-5-methylisoxazole-4-carboxylic acid and methyl 2-amino-5-chloro-4-(piperazin-1-yl)benzoate (TFA salt) were coupled under the conditions described in Preparation M to give methyl 2-amino-5-chloro-4-(4-(3-(2-methoxyphenyl)-5-methylisoxazole-4-carbonyl)piperazin-1-yl)benzoate. 1H-NMR (CDCl3, 400 MHz): δ 7.82 (1H, s), 7.60-7.47 (2H, m), 7.13-6.97 (2H, m), 6.01 (1H, s), 3.85 (3H, s), 3.84 (2H, s), 3.80 (3H, s), 3.25 (2H, s), 2.99 (2H, s), 2.58 (3H, s), 2.42 (2H, s).

Workup

  1. customdescribed in Preparation M

Sources & evidence

ORD record
ord-0ea6e755639e4e1f91f33787008c0f79
Source dataset
uspto-grants-2013_01
Patent number
US08362004B2

Reaction notes

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