Sodium cyanoborohydride → HCID 178445778, compound

HRID 713868Notes

Reaction equation

HRID 713868 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[C:13]([C:24]([F:27])([F:26])[F:25])=[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].[NH2:28][CH2:29][CH2:30][C:31]([NH:33][S:34]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)(=[O:36])=[O:35])=[O:32].[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[C:13]([C:24]([F:25])([F:26])[F:27])=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:28][CH2:29][CH2:30][C:31]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)(=[O:36])=[O:35])=[O:32])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 669264473-amino-N-(phenylsulfonyl)propanamideHCID 178445788HCID 178445788, compound

Product 1

HCID 178445778HCID 178445778, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

6-(trans-4-tert-butylcyclohexyloxy)-5-(trifluoromethyl)-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)-5-(trifluoromethyl)naphthalen-2-yl)methylamino)-N-(phenylsulfonyl)propanamide as a white solid. 120 mg, white solid, 53%. ESI-MS: 591.0 (M+H)+. HPLC: 98.05%. 1H NMR (400 MHz, DMSO-d6) δ: 8.22˜8.13 (m, 1H), 8.11˜8.04 (m, 2H), 7.789˜7.63 (m, 4H), 7.45˜7.30 (m, 3H), 4.63˜4.49 (m, 1H), 4.27 (s, 2H), 2.99 (t, 2H), 2.32 (t, 2H), 2.19˜2.07 (m, 2H), 1.85˜1.74 (m, 2H), 1.45˜1.30 (m, 2H), 125˜1.12 (m, 2H), 1.10˜0.97 (m, 1H), 0.86 (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)

Sources & evidence

ORD record
ord-90e2953c18e5488f9a0c7f30024cd75e
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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