1,1'-Carbonyldiimidazole → HCID 12041757, compound

HRID 1263627Notes

Reaction equation

HRID 1263627 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][OH:14])[O:9]2)=[CH:4][CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16]>C1COCC1>[OH:14][CH2:13][CH:8]1[O:9][C:10]2[C:5](=[CH:4][CH:3]=[C:2]3[NH:1][C:15](=[O:16])[NH:12][C:11]3=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 12041756HCID 12041756, compound

Product 1

HCID 12041757HCID 12041757, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (7,8-diamino-chroman-2-yl)-methanol (194 mg, 1 mmol) in THF (50 mL) was added 1,1′-carbonyidiimidazole (CDI) (81 mg, 1.5 mmol). The resulting solution was stirred for 8 hours at room temperature and the solvent was evaporated in vacuo to a residue. The residue was purified by chromatography (50% CH2Cl2-hexanes) to give 139 mg (63% yield) of the title compound: mp 240° C.; 1H NMR (400 MHz, CDCl3) δ1.65 (m, 1H), 2.01 (m, 1H), 2.70 (m, 2H), 3.55 (m, 1H), 3.63 (m, 1H), 4.05 (m, 1H), 4.68 (bs, 1H, OH), 6.41 (d, J=7.9, 1H), 6.60 (d, J=7.9, 1H), 10.36 (s, 1H), 10.37 (s, 1H); IR: 3250, 3080, 2980, 1700, 1500, 1210 cm−1; MS 220 [M]+.

Workup

  1. customthe solvent was evaporated in vacuo to a residue
  2. customThe residue was purified by chromatography (50% CH2Cl2-hexanes)

Sources & evidence

ORD record
ord-382a57ad825340a3941a7505224f6718
Source dataset
uspto-grants-2003_04
Patent number
US06541501B2

Reaction notes

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