Triethylamine → HCID 86758604, compound

HRID 1018380Notes

Reaction equation

[C:1]12([O:11][CH2:12][C:13]3[NH:17][C:16]([CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)=[N:15][C:14]=3[C:24]([NH:26][C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=3)[C:30](O)=[O:31])=[O:25])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Cl.[CH2:37]([O:44][NH2:45])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(N(CC)CC)C>>[CH2:37]([O:44][NH:45][C:30]([C:29]1[CH:28]=[C:27]([NH:26][C:24]([C:14]2[N:15]=[C:16]([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]3)[NH:17][C:13]=2[CH2:12][O:11][C:1]23[CH2:2][CH:3]4[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]4)[CH2:8]2)[CH2:10]3)=[O:25])[CH:35]=[CH:34][CH:33]=1)=[O:31])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

Reactant 3

HCID 8471Triethylamine

HCID 102312Benzyloxyamine hydrochloride

HCID 9832467HCID 9832467, compound

Product 1

HCID 86758604HCID 86758604, compoundYield 84%

Procedure

3-{[5-(Adamantan-1-yloxymethyl)-2-cyclohexyl-1H-imidazole-4-carbonyl]-amino}-benzoic acid (Example 216) (910 mg, 1.90 mmol) was reacted with O-benzylhydroxylamine hydrochloride (455 mg, 2.85 mmol) in the presence of triethylamine (0.40 ml, 2.85 mmol) according to the procedure of Example 20, step d. The crude material was purified by flash column chromatography (silica, DCM/methanol 95:5) to afford a colourless foam (910 mg, 84%). 1H NMR (300MHz, CDCl3) 9.25 (1H, br s), 9.06 (1H, s), 8.64 (1H, s), 8.01 (1H, s), 7.84 (1H, m), 7.41 (6H, m), 5.06 (2H, s), 4.98 and 4.81 (2H, 2×s), 2.72 (1H, m), 2.19 (3H, br s), 2.07 (2H, m), 1.90-1.36 (20H, m).

Workup

customThe crude material was purified by flash column chromatography (silica, DCM/methanol 95:5)

Sources & evidence

ORD record: ord-73551743d99a451aa76b897be5cc85f5
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06479531B1

Reaction notes

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