Sodium Carbonate → HCID 178513253, 화합물

HRID 1051040노트

반응식

HRID 1051040 반응식
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[Na+].[Na+].[OH:10][C@@H:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([C:20]#[N:21])[C:14]=2[CH2:13][CH2:12]1>CCO>[OH:3][NH:2][C:20]([C:15]1[C:14]2[CH2:13][CH2:12][C@H:11]([OH:10])[C:19]=2[CH:18]=[CH:17][CH:16]=1)=[NH:21]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 14515308HCID 14515308, 화합물

생성물 1

HCID 178513253HCID 178513253, 화합물수율 90%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To hydroxylamine hydrochloride (0.87 g, 12.5 mmol) and sodium carbonate (1.32 g, 12.5 mmol) in EtOH (20 mL) was added (S)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile INT-2 (1.59 g, 10 mmol) in one portion and the solution was heated to reflux. After 16 h, the reaction was cooled and filtered to remove the solids. The EtOH was removed and the compound purified by chromatography (MeOH/DCM) to give 1.74 g (90%) of (S)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide INT-3 as a white foam. LCMS-ESI (m/z) calculated for C10H12N2O2: 192.1. found: 193.1 [M+H]+, tR=0.56 min. 1H NMR (400 MHz, MeOD) δ 10.30 (s, 1H), 9.97 (s, 1H), 7.72-7.58 (m, 1H), 7.46-7.37 (m, 2H), 5.22 (t, J=6.5, 1H), 3.17-3.03 (m, 1H), 2.99-2.83 (m, 1H), 2.49 (dddd, J=11.4, 8.0, 7.0, 4.4, 1H), 2.02-1.88 (m, 1H). (R)-N,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide is made in an analogous fashion from (R)-1-hydroxy-2,3-dihydro-1H-indene-4-carbonitrile.

후처리

  1. temperaturethe solution was heated to reflux
  2. temperaturethe reaction was cooled
  3. filtrationfiltered
  4. customto remove the solids
  5. customThe EtOH was removed
  6. customthe compound purified by chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-8f71c31752df481bba2f835c9c7ba914
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388147B2

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