Reacción #11094

ord-02cb432b381b4fc7ae5a7f95794986bb

Ecuación de reacción

CC(C)(C)OC(=O)NC(=N)c1ccc(CNC(=O)[C@@H]2CCc3ncc(NS(C)(=O)=O)c(=O)n32)cc1

(S)-[imino-(4-{[(3-methanesulfonylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl)-phenyl)-methyl]-carbamic acid tert-butyl ester

CCN(CC)c1cnc2n(c1=O)[C@H](C(=O)NCc1ccc(C(=N)NC(=O)OC(C)(C)C)cc1)CC2

intermediate 3a

(S)-[(4-{[(3-diethylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

4-acetylbenzene sulfonyl chloride

→

CC(=O)c1ccc(S(=O)(=O)Nc2cnc3n(c2=O)[C@H](C(=O)NCc2ccc(C(=N)NC(=O)OC(C)(C)C)cc2)CC3)cc1

35a

Rendimiento 42.0%

(S)-{[4-({[3-(4-acetyl-benzenesulfonylamino)-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl]-amino}-methyl)-phenyl]-imino-methyl}-carbamic acid tert-butyl ester

Rendimiento 42.0%

Reactantes

16a

(S)-[imino-(4-{[(3-methanesulfonylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl)-phenyl)-methyl]-carbamic acid tert-butyl ester

intermediate 3a

(S)-[(4-{[(3-diethylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carbonyl)-amino]-methyl}-phenyl)-imino-methyl]-carbamic acid tert-butyl ester

4-acetylbenzene sulfonyl chloride

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Procedimiento

Following a procedure similar to that for the preparation of 16a, intermediate 3a (50 mg, 0.117 mmol) and 4-acetylbenzene sulfonyl chloride (30.6 mg, 0.14 mmol) yielded 30.0 mg (42.0%) of 35a. MS (ESI) 609.1 (M+H+).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07094783B2uspto-grants-2006_08