HCID 69651826, compound → HCID 21957565, compound

HRID 2213548Notes

Reaction equation

HRID 2213548 reaction equation
CO[C:3]([C:5]1[N:6]([CH:22]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:7]=[N:8][C:9]=1[CH2:10][O:11][C:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH2:13]1)[CH2:19]2)=[O:4].C[O:30][C:31](=[O:62])[C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([NH:38]C(C2C(COC3C=CC=CC=3)=NN(C3C(Cl)=CC=CC=3Cl)N=2)=O)[CH:33]=1>>[C:12]12([O:11][CH2:10][C:9]3[N:8]=[N:7][N:6]([CH:22]4[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)[C:5]=3[C:3]([NH:38][C:34]3[CH:33]=[C:32]([CH:37]=[CH:36][CH:35]=3)[C:31]([OH:62])=[O:30])=[O:4])[CH2:19][CH:18]3[CH2:20][CH:14]([CH2:15][CH:16]([CH2:17]3)[CH2:21]1)[CH2:13]2

Participants

3

Reactant 2

HCID 69651826HCID 69651826, compoundHCID 69652076HCID 69652076, compound

Product 1

HCID 21957565HCID 21957565, compound

Procedure

5-(Adamantan-1-yloxymethyl)-3-cycloheptyl-3H-[1,2,3]triazole-4-carboxylic acid methyl ester was converted to the corresponding acid (as in Example 28, step c) which was then coupled to methyl 3-aminobenzoate (as in Example 28, step d). Hydrolysis of the methyl ester (as in Example 28, step e) resulted in the preparation of 3-{[5-(adamantan-1-yloxymethyl)-3-cycloheptyl-3H-[1,2,3]triazole-4-carbonyl]-amino}-benzoic acid. 1H NMR (d6-DMSO) 13.02 (1H, s), 10.64 (1H, s), 8.29 (1H, s), 7.89 (1H, d, J=9 Hz), 7.73 (1H, d, J=6 Hz), 7.54-7.49 (1H, m), 4.96-4.92 (1H, m), 4.73 (2H, s), 2.10-2.02 (7H, m), 1.78-1.45 (20H, m). The material was further analysed as its N-methyl D-glucamine salt.

Sources & evidence

ORD record
ord-283ff4b260b9417a976744db1b261f7a
Source dataset
uspto-grants-2006_09
Patent number
US07105558B2

Reaction notes

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