Diisopropylethylamine → (R)-1-(4-Fluorophenyl)-4a-methoxymethyl-6-[(1S,4S)-6-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)pyridine-3-sulfonyl]-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

HRID 1907299Notes

Reaction equation

HRID 1907299 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:20][CH2:19][C:18]3[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]4[CH:23]=[N:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:16]=4[CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Cl.[C@H:44]12[CH2:50][C@H:47]([NH:48][CH2:49]1)[CH2:46][O:45]2>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[C:16]3[CH:17]=[C:18]4[C@:13]([CH2:31][O:32][CH3:33])([CH2:14][C:15]=3[CH:23]=[N:22]2)[CH2:12][N:11]([S:8]([C:5]2[CH:6]=[N:7][C:2]([N:48]3[CH2:49][C@@H:44]5[CH2:50][C@H:47]3[CH2:46][O:45]5)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:20][CH2:19]4)=[CH:25][CH:26]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 21303398(1S,4S)-2-oxa-5-azabicyclo(2.2.1)heptane hydrochlorideHCID 86669986HCID 86669986, compound

Product 1

HCID 68069687(R)-1-(4-Fluorophenyl)-4a-methoxymethyl-6-[(1S,4S)-6-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)pyridine-3-sulfonyl]-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

Procedure

The title compound was prepared by the method of Example 20 using (R)-6-(6-chloropyridine-3-sulfonyl)-4a-methoxymethyl-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triazacyclopenta[b]naphthalene, diisopropylethylamine and (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane hydrochloride. LCMS (Method F): 552 (M+H)+, Retention time 4.7 minutes.

Sources & evidence

ORD record
ord-71f4c7d00ad84609aa0037f7fc379ca8
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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