Sodium cyanoborohydride → HCID 178445776, compound

HRID 2404120Notes

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

Participants

Conditions

Temperature: 80 °C

Procedure

6-((trans)-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (300 mg, 0.96 mmol, 1 equiv) and 3-amino-N-(methylsulfonyl)propanamide (239 mg, 1.19 mmol, 1.5 equiv) were dissolved in anhydrous EtOH. 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 prep-TLC to give 3-((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)-N-(methylsulfonyl)propanamide as a white solid (62 mg, 14%). (mobile phase: CH3OH/DCM=1:10). ESI-MS (M+1)+: 461.2, HPLC: 96.38%. 1H NMR (400 MHz, DMSO-d6) δ: 7.93 (s, 1H), 7.85˜7.77 (m, 2H), 7.59˜7.49 (m, 1H), 7.43˜7.35 (m, 1H), 7.20˜7.11 (m, 1H), 4.45˜4.33 (m, 1H), 4.20 (s, 2H), 2.98 (t, 2H), 2.77 (s, 3H), 2.35 (t, 2H), 2.26˜2.14 (m, 2H), 1.86˜1.75 (m, 2H), 1.41˜1.30 (m, 2H), 1.27˜1.14 (m, 2H), 1.13˜1.02 (m, 1H), 0.89 (s, 9H).

Workup

stirringstirred at 80° C. for 16 h
concentrationThe organic layer was concentrated
custompurified by prep-TLC

Sources & evidence

ORD record: ord-cdab7405f4d544d5b21a2ac18ec16bcf
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802659B2

Reaction notes

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