Methyl Anthranilate → 2-[(2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carbonyl)-amino]-benzoic acid methyl ester

HRID 1018304Notes

Reaction equation

[C:1]12([CH2:11][C:12]3[NH:13][C:14]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][C:16]=3[C:17](O)=[O:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH2:35]>>[CH3:26][O:27][C:28](=[O:36])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH:35][C:17]([C:16]1[CH:15]=[C:14]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:13][C:12]=1[CH2:11][C:1]12[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2)=[O:18]

Participants

Reactant 2

HCID 8635Methyl Anthranilate

HCID 113820842-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid

Product 1

HCID 570313572-[(2-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carbonyl)-amino]-benzoic acid methyl esterYield 33.1%

Procedure

2-Adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carboxylic acid (Example 1, step c) (335 mg, 1.00 mmol) was reacted with 2-amino-benzoic acid methyl ester (1.51 mg, 1.00 mmol) according to the procedure of Example 1, step d to afford the product as a pale yellow solid (155 mg, 33%). 1H NMR (300 MHz, d6-DMSO) 11.32 (1H, s), 11.24 (1H, s), 8.67 (1H, d), 8.00 (1H, d) 7.60 (3H, m), 7.40 (2H, m), 7.25 (1H, t), 7.12 (1H, t), 6.83 (1H, s), 3.92 (3H, s), 2.86 (2H, s), 1.88 (3H, s), 1.55 (12H, m).

Sources & evidence

ORD record: ord-d982b8845f544bfa83ad22fcd1b14217
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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