Bromomethylcyclopropane → (R)-4a-Cyclopropylmethoxymethyl-1-(4-fluorophenyl)-6-(6-morpholin-4-yl-pyridine-3-sulfonyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene

HRID 1907300Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]3[CH:13]=[C:14]4[C@:19]([CH2:21][OH:22])([CH2:20][C:11]=3[CH:10]=[N:9]2)[CH2:18][N:17]([S:23]([C:26]2[CH:27]=[N:28][C:29]([N:32]3[CH2:37][CH2:36][O:35][CH2:34][CH2:33]3)=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:16][CH2:15]4)=[CH:4][CH:3]=1.[CH:38]1([CH2:41]Br)[CH2:40][CH2:39]1>>[CH:38]1([CH2:41][O:22][CH2:21][C@@:19]23[CH2:18][N:17]([S:23]([C:26]4[CH:27]=[N:28][C:29]([N:32]5[CH2:37][CH2:36][O:35][CH2:34][CH2:33]5)=[CH:30][CH:31]=4)(=[O:24])=[O:25])[CH2:16][CH2:15][C:14]2=[CH:13][C:12]2[N:8]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[N:9]=[CH:10][C:11]=2[CH2:20]3)[CH2:40][CH2:39]1

Participants

Reactant 2

HCID 81503Bromomethylcyclopropane

HCID 66780233[(R)-1-(4-Fluorophenyl)-6-[[6-(4-morpholinyl)-3-pyridinyl]sulfonyl]-1,4,7,8-tetrahydro-1,2,6-triazacyclopenta[b]naphthalen-4a-yl]methanol

Product 1

HCID 56849161(R)-4a-Cyclopropylmethoxymethyl-1-(4-fluorophenyl)-6-(6-morpholin-4-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 Preparation 25b using [(R)-1-(4-fluorophenyl)-6-[[6-(4-morpholinyl)-3-pyridinyl]sulfonyl]-1,4,7,8-tetrahydro-1,2,6-triazacyclopenta[b]naphthalen-4a-yl]methanol and cyclopropylmethyl bromide. 1H NMR (400 MHz, CHCl3-d): δ 8.54 (d, 1H), 7.80 (dd, 1H), 7.51-7.39 (m, 3H), 7.14 (t, 2H), 6.62 (d, 1H), 4.17 (dd, 1H), 3.80 (t, 4H), 3.65 (t, 4H), 3.45 (d, 1H), 3.30 (dd, 2H), 3.27-3.14 (m, 2H), 2.75-2.65 (m, 1H), 2.43-2.33 (m, 2H), 2.21-2.10 (m, 1H), 2.10 (d, 1H), 1.12-1.01 (m, 1H), 0.49 (dd, 2H), 0.26-0.15 (m, 2H).

Sources & evidence

ORD record: ord-84170e77e2854cf184b90527e2e6af2f
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598154B2

Reaction notes

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