Pyridine-3-sulfonyl chloride → (R)-4a-Ethoxymethyl-1-(4-fluorophenyl)-6-[[3-pyridinyl]sulfonyl]-1,4,7,8-tetrahydro-1,2,6-triazacyclopenta[b]naphthalene

HRID 1907277Notes

Reaction equation

C(OC([N:8]1[CH2:17][CH2:16][C:15]2[C@:10]([CH2:28][O:29][CH2:30][CH3:31])([CH2:11][C:12]3[CH:20]=[N:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:13]=3[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:33]=1>>[CH2:30]([O:29][CH2:28][C@@:10]12[CH2:9][N:8]([S:38]([C:34]3[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=3)(=[O:40])=[O:39])[CH2:17][CH2:16][C:15]1=[CH:14][C:13]1[N:18]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[N:19]=[CH:20][C:12]=1[CH2:11]2)[CH3:31]

Participants

Reactant 2

HCID 3164136Pyridine-3-sulfonyl chloride

HCID 66780480(R)-4a-Ethoxymethyl-1-(4-fluorophenyl)-1,4,4a,5,7,8-hexahydro-1,2,6-triazacyclopenta[b]naphthalene-6-carboxylic acid tert-butyl ester

Product 1

HCID 56848864(R)-4a-Ethoxymethyl-1-(4-fluorophenyl)-6-[[3-pyridinyl]sulfonyl]-1,4,7,8-tetrahydro-1,2,6-triazacyclopenta[b]naphthalene

Procedure

The title compound was prepared by the method of Preparation 1c using (R)-4a-ethoxymethyl-1-(4-fluorophenyl)-1,4,4a,5,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-6-carboxylic acid tert-butyl ester and pyridine-3-sulfonyl chloride. LCMS (Method C): 469 (M+H)+, Retention time 11.1 minutes.

Sources & evidence

ORD record: ord-f8b3cfa1d8e44805bbe9d4b52ddbeff2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598154B2

Reaction notes

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