1H-imidazole-2-carbaldehyde → HCID 54223994, compound

HRID 842112Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:10][C:11]2[O:12][C:13]3[C:19]([NH2:20])=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:26]1[CH:30]=[CH:29][N:28]=[C:27]1[CH:31]=O.C([BH3-])#N.[Na+]>>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=2[O:24][CH3:25])[CH2:10][C:11]2[O:12][C:13]3[C:19]([NH:20][CH2:31][C:27]4[NH:26][CH:30]=[CH:29][N:28]=4)=[CH:18][CH:17]=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 249551H-imidazole-2-carbaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 9880976HCID 9880976, compound

Product 1

HCID 54223994HCID 54223994, compoundYield 31.4%

Procedure

By employing a procedure similar to that in Example 33 and using 2-(3-cyclopentyloxy-4-methoxybenzyl)-7-aminobenzoxazole (1.3 g, 0.0038 mol), imidazole-2-carboxaldehyde (0.54 g, 0.0056 mol) and sodium cyanoborohydride (0.38 g, 0.0060 mol), a yellow oil was obtained after workup. The oil was triturated with a 50:50 blend of hexane in ether and the solid product (0.5 g) which was obtained, was separated by filtration. This solid could be recrystallized from ethanol (1 g/14 ml) to give the title compound as white crystals, mp 179-180° C.

Workup

customa yellow oil was obtained after workup
customThe oil was triturated with a 50:50 blend of hexane in ether

Sources & evidence

ORD record: ord-a87460299c89420781652f7ac1a064b0
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372770B1

Reaction notes

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