Hydrochloric Acid → HCID 57968790, 화합물

HRID 1471611노트

반응식

HRID 1471611 반응식
[NH2:1][CH2:2][C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:17]=[CH:16][C:11]3[B:12]([OH:15])[O:13][CH2:14][C:10]=3[CH:9]=2)=[CH:5][CH:4]=1.[CH:20]1([CH:26]=O)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[BH4-].[Na+].Cl>CCO>[CH:20]1([CH2:26][NH:1][CH2:2][C:3]2[CH:19]=[CH:18][C:6]([O:7][C:8]3[CH:17]=[CH:16][C:11]4[B:12]([OH:15])[O:13][CH2:14][C:10]=4[CH:9]=3)=[CH:5][CH:4]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 16275CyclohexanecarboxaldehydeHCID 4311764Sodium borohydrideHCID 57968923Crisaborole intermediate

생성물 1

HCID 57968790HCID 57968790, 화합물

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 5-(4-aminomethyl-phenoxy)-3H-benzo[c][1,2]oxaborol-1-ol (150 mg, 0.59 mmol, 1.0 eq.) in EtOH (5.0 mL) was added cyclohexanecarbaldehyde (280 μL, 2.36 mmol, 4.0 eq.). The mixture was stirred at room temperature for 30 minutes. After cooling to 0° C., NaBH4 (89 mg, 0.36 mmol, 4.0 eq.) was added in portions and the mixture was allowed to warm to room temperature and stirred for 2 h. The mixture was carefully treated with dilute HCl (5 mL) and aqueous phase was extracted with EtOAc (3×10 mL). Combined organic extracts was washed with brine (10 mL), dried over MgSO4, filtered and the filtrate was concentrated under reduced pressure. The residue was applied to silica chromatography eluting with MeOH/DCM (0:100 to 10:90) to give 5-{4-[(cyclohexylmethyl-amino)-methyl]-phenoxy}-3H-benzo[c][1,2]oxaborol-1-ol as a white solid. LCMS (m/z) 352 (M+H); 1H NMR (DMSO-d6) δ: 9.08 (s, 1H), 7.68 (d, J=8.0 Hz, 1H), 7.30-7.37 (m, J=8.5 Hz, 2H), 6.95-7.02 (m, 2H), 6.88-6.95 (m, 2H), 4.89 (s, 2H), 3.64 (s, 2H), 2.31 (d, J=6.6 Hz, 2H), 1.67-1.77 (m, 2H), 1.56-1.66 (m, 3H), 1.30-1.44 (m, 1H), 1.02-1.23 (m, 3H), 0.77-0.91 (m, 2H).

후처리

  1. temperatureAfter cooling to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 2 h
  4. extractionwas extracted with EtOAc (3×10 mL)
  5. washCombined organic extracts was washed with brine (10 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. washeluting with MeOH/DCM (0:100 to 10:90)

출처 및 근거

ORD 기록
ord-b8a1cab6628f44f68469afac647ff6b8
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012431B2

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