Ethanolamine → [(S)-2-[7-(2-Hydroxyethylcarbamoyl)-furo[2,3-g]indazol-1-yl]-1-methylethyl]-carbamic acid benzyl ester

HRID 1453896Notes

Reaction equation

HRID 1453896 reaction equation
C(O[C:9]([C:11]1[O:36][C:14]2=[CH:15][CH:16]=[C:17]3[C:21]([N:20]([CH2:22][C@@H:23]([NH:25][C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH3:24])[N:19]=[CH:18]3)=[C:13]2[CH:12]=1)=[O:10])C1C=CC=CC=1.[Cl-].[NH4+].[CH2:39]([CH2:41][NH2:42])[OH:40]>>[CH2:29]([O:28][C:26](=[O:27])[NH:25][C@@H:23]([CH3:24])[CH2:22][N:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]3[O:36][C:11]([C:9](=[O:10])[NH:42][CH2:41][CH2:39][OH:40])=[CH:12][C:13]3=2)[CH:18]=[N:19]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 700EthanolamineHCID 25517Ammonium ChlorideHCID 688563631-((S)-2-Benzyloxycarbonylaminopropyl)-1H-furo[2,3-g]indazole-7-carboxylic acid benzyl ester

Product 1

HCID 68854656[(S)-2-[7-(2-Hydroxyethylcarbamoyl)-furo[2,3-g]indazol-1-yl]-1-methylethyl]-carbamic acid benzyl esterYield 57%

Procedure

A stirred solution of the product from Step A, Example 2 (0.44 g, 0.91 mmol) in ethanolamine was heated at 80° C. for 8 h. A saturated aqueous solution of ammonium chloride (20 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined extracts were washed with brine, dried and evaporated to a residue, which was purified by chromatography (silica, 60% ethyl acetate in hexane) to give an oil (0.23 g, 57%): MS (ES) m/z 437 (M+); 1H NMR (CDCl3) δ 8.00 (s, 1H), 7.69 (d, 1H, J=8.0 Hz), 7.22-7.30 (m, 7H), 5.30 (brs, 1H), 5.03 (m, 2H), 4.63 (m, 1H), 4.40 (m, 1H), 4.15 (m, 1H), 3.85 (m, 2H), 3.65 (m, 2H), 1.26 (d, 3H, J=8.0 Hz).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined extracts were washed with brine
  3. customdried
  4. customevaporated to a residue, which
  5. customwas purified by chromatography (silica, 60% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-91d82bcd26e8434dacb268bc757701ff
Source dataset
uspto-grants-2009_01
Patent number
US07476687B2

Reaction notes

Loading…