HCID 69651910, compound → HCID 21957557, compound

HRID 2213549Notes

Reaction equation

CO[C:3]([C:5]1[NH:6][NH:7][N:8]([CH:22]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[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]([CH:22]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[NH:7][NH:6][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])[CH2:13][CH:14]3[CH2:15][CH:16]([CH2:17][CH:18]([CH2:20]3)[CH2:19]1)[CH2:21]2

Participants

Reactant 2

HCID 69651910HCID 69651910, compound

HCID 69652076HCID 69652076, compound

Product 1

HCID 21957557HCID 21957557, compound

Procedure

5-(Adamantan-1-yloxymethyl)-1-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)-1-cycloheptyl-3H-[1,2,3]triazole-4-carbonyl]-amino}-benzoic acid. 1H NMR (d6-DMSO) 12.91 (1H, s), 10.62 (1H, s), 8.51 (1H, m), 7.98-7.95 (1H, m), 7.68 (1H, d, J=9 Hz), 7.47-7.42 (1H, m), 4.98 (2H, s), 4.71-4.66 (1H, m), 2.48-2.07 (7H, m), 1.80-1.54 (20H, m). The material was further analysed as its N-methyl D-glucamine salt.

Sources & evidence

ORD record: ord-9a42a9099d3141b3add0ddffe4d6e7fc
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07105558B2

Reaction notes

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