Diisopropylethylamine → N-[4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-yl]-2-methyl-isonicotinamide

HRID 51854Notes

Reaction equation

HRID 51854 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH2:12])[S:11][C:7]=2[C:6]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][O:16]3)=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.Cl.[CH3:30][C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][N:39]=1)[C:34](Cl)=[O:35]>C1COCC1.ClCCl>[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([NH:12][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][N:39]=[C:31]([CH3:30])[CH:32]=3)[S:11][C:7]=2[C:6]([N:13]2[CH2:18][C@@H:17]3[CH2:19][C@H:14]2[CH2:15][O:16]3)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 213034014-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamineHCID 219192182-Methyl-isonicotinoyl chloride hydrochloride

Product 1

HCID 10216096N-[4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-yl]-2-methyl-isonicotinamideYield 90%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 111 mg (0.40 mmol) 4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamine and 0.26 ml (1.50 mmol) N-ethyldiisopropylamine in 20 ml THF at room temperature was added dropwise a solution of 127 mg (0.66 mmol) 2-methyl-isonicotinoyl chloride hydrochloride in 20 ml dichloromethane and stirring continued at room temperature for 24 h. The reaction mixture was then concentrated in vacuo. Flash chromatography (3/97 methanol/ethyl acetate) followed by trituration in ether afforded 142 mg (90%) N-[4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-yl]-2-methyl-isonicotinamide as a yellow crystalline solid. ES-MS m/e (%): 419 (M+Na+, 17), 397 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-e7dba4fae4b1416495240e12b8ec35fe
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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