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

HRID 1907285Notes

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][CH2:33][CH3:34])([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.[CH3:35][NH2:36]>>[CH2:33]([O:32][CH2:31][C@@:13]12[CH2:12][N:11]([S:8]([C:5]3[CH:6]=[N:7][C:2]([NH:36][CH3:35])=[CH:3][CH:4]=3)(=[O:10])=[O:9])[CH2:20][CH2:19][C:18]1=[CH:17][C:16]1[N:21]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:22]=[CH:23][C:15]=1[CH2:14]2)[CH3:34]

Participants

Reactant 2

HCID 6329Methylamine

HCID 86669985HCID 86669985, compound

Product 1

HCID 56848921(R)-4a-Ethoxymethyl-1-(4-fluorophenyl)-6-[[6-methylamino-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 4b using (R)-6-(6-chloropyridine-3-sulfonyl)-4a-ethoxymethyl-1-(4-fluorophenyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triazacyclopenta[b]naphthalene and methylamine. LCMS (Method B): 498 (M+H)+, Retention time 3.6 minutes.

Sources & evidence

ORD record: ord-274f3811180e4888a3e238e774f5d06e
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598154B2

Reaction notes

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