1,4-dithia-7-azaspiro [4.4]nonane-8(S)-carboxylic acid, methyl ester hydrobromide → 7-[5-(3-Phenylpropyl)-1H-imidazole-2-carbonyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid methyl ester

HRID 862230Notes

Reaction equation

HRID 862230 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][C:10]2[N:11]=[C:12]([C:15]([OH:17])=O)[NH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.[CH3:19][O:20][C:21]([C@@H:23]1[CH2:31][C:26]2([S:30][CH2:29][CH2:28][S:27]2)[CH2:25][NH:24]1)=[O:22]>>[CH3:19][O:20][C:21]([C@@H:23]1[CH2:31][C:26]2([S:27][CH2:28][CH2:29][S:30]2)[CH2:25][N:24]1[C:15]([C:12]1[NH:11][C:10]([CH2:9][CH2:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:14][N:13]=1)=[O:17])=[O:22]

Participants

3

Reactant 2

HCID 132746721,4-dithia-7-azaspiro [4.4]nonane-8(S)-carboxylic acid, methyl ester hydrobromideHCID 178524887HCID 178524887, compound

Product 1

HCID 537702227-[5-(3-Phenylpropyl)-1H-imidazole-2-carbonyl]-1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid methyl ester

Procedure

4-(3-Phenylpropyl)imidazole-2-carboxylic acid (13d) was coupled to 1,4-dithia-7-azaspiro[4.4]nonane-8(S)-carboxylic acid methyl ester hydrobromide (Smith et. al., J. Med. Chem., 31, pp. 875-85 (1988)) by the method described for 23 to afford 140 mg (65%) as a yellow gum: 1H NMR (CDCl3) δ 7.34-7.15 (5H, m), 6.98-6.8 (1H, 3 s), 5.7-5.65 (0.5 H, m), 5.2-5.1 (1H,m), 4.82-4.75 (0.5H, m), 4.4-4.35 (1H, m), 4.05 (1H,d), 3.75-3.7 (3H, 2 s), 3.4-3.3 (4H,m), 2.95-2.45 (8H, m), 2.05-1.95 (2H,m).

Workup

  1. customto afford 140 mg (65%) as a yellow gum

Sources & evidence

ORD record
ord-6e1b2c3f97064c06a9782a7a914e5a7f
Source dataset
uspto-grants-1998_02
Patent number
US05716929

Reaction notes

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