Triethylamine → 3-Pyridinemethanamine

HRID 1746414Notes

Reaction equation

C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]2[CH2:28][O:27]2)=[CH:22][CH:21]=1)(=[O:19])=[O:18].[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][NH2:40])[CH:34]=1>C(O)C>[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][NH2:40])[CH:34]=1.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[N:16]([CH2:29][CH:30]([CH3:32])[CH3:31])[S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]([OH:27])[CH2:28][NH:40][CH2:39][C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)=[CH:22][CH:21]=1)(=[O:18])=[O:19]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of pyridin-3-ylmethanamine (10.38 mg, 0.096 mmol) in ethanol (0.25 mL) was prepared in a 4 mL reaction vial and triethylamine (0.027 mL, 0.192 mmol) added. A solution of N-(2,4-dimethylphenyl)-N-isobutyl-4-(oxiran-2-yl)benzenesulfonamide (28.8 mg, 0.08 mmol) in ethanol (0.75 mL) was then added and the reaction heated at 40° C. overnight. After this time, further pyridin-3-ylmethanamine (10.38 mg, 0.096 mmol) was added and the reaction heated at 50° C. for an additional 2 hours. The reaction mixture was then concentrated under a stream of nitrogen and the crude mixture purified by high-pH MDAP to give the required product, 10.6 mg. LCMS (M+1) 468, RT 1.24 mins.

Workup

temperaturethe reaction heated at 50° C. for an additional 2 hours
concentrationThe reaction mixture was then concentrated under a stream of nitrogen
customthe crude mixture purified by high-pH MDAP

Sources & evidence

ORD record: ord-62f5d19c99b143cba361f330451ee4ae
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150508B2

Reaction notes

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