Sodium cyanoborohydride → HCID 178445777, compound

HRID 2404086Notes

Reaction equation

HRID 2404086 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH:22]=O)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH2:24][CH2:25][CH2:26][C:27]([NH:29][S:30]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:32])=[O:31])=[O:28].[BH3-]C#N.[Na+]>C(O)C>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:24][CH2:25][CH2:26][C:27]([NH:29][S:30]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:32])=[O:31])=[O:28])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 669264473-amino-N-(phenylsulfonyl)propanamideHCID 178445787HCID 178445787, compound

Product 1

HCID 178445777HCID 178445777, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-(Trans-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (300 mg, 0.96 mmol, 1 equiv) and 3-amino-N-(phenylsulfonyl)propanamide (1.19 mmol, 1.5 equiv) were dissolved in anhydrous ethanol. The mixture was stirred at 80° C. for 1 h. Then NaBH3CN (110 mg, 1.74 mmol, 2 equiv) was added to the mixture and stirred at 80° C. for 16 h. The organic layer was concentrated and purified by preparative thin layer chromatography (mobile phase was methanol:dichloromethane 1:10) to give 3-((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)-N-(phenylsulfonyl)propanamideas a white solid. 284 mg, white solid, 62%. ESI-MS: 523.0 (M+H)+. HPLC: 99.42%. 1H NMR (400 MHz, DMSO-d6) δ: 7.91 (s, 1H), 7.85˜7.82 (m, 2H), 7.74˜7.72 (m, 2H), 7.53˜7.51 (m, 1H), 7.41˜7.35 (m, 4H), 7.20˜7.15 (m, 1H), 4.45˜4.40 (m, 1H), 4.23 (s, 2H), 2.99 (t, 2H), 2.33 (t, 2H), 2.28˜2.16 (m, 2H), 1.89˜1.78 (m, 2H), 1.41˜1.31 (m, 2H), 1.27˜1.17 (m, 2H), 1.13˜1.06 (m, 1H), 0.89 (s, 9H).

Workup

  1. stirringstirred at 80° C. for 16 h
  2. concentrationThe organic layer was concentrated
  3. custompurified by preparative thin layer chromatography (mobile phase was methanol:dichloromethane 1:10)
  4. customto give 3-((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)-N-(phenylsulfonyl)propanamideas a white solid

Sources & evidence

ORD record
ord-eb0e6eef65d248909fccd9d311c6a1c8
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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