1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine → HCID 54767677, compound

HRID 1503293Notes

Reaction equation

[OH:1][CH:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH2:33][C@@H:34]([OH:37])[CH2:35][OH:36])=[CH:8][N:9]2[C:14]1[CH:32]=[CH:31][C:17]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:27]([F:30])([F:29])[F:28])=[C:23]([CH:26]=2)[C:24]#[N:25])=[CH:16][CH:15]=1)[CH2:3][OH:4].CC[C@H]1[C@H]2C[C@H]([C@H](OC3C4C(=CC=CC=4)C(O[C@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1>>[OH:1][CH:2]([C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([CH2:33][C@H:34]([OH:37])[CH2:35][OH:36])=[CH:8][N:9]2[C:14]1[CH:32]=[CH:31][C:17]([O:18][C:19]2[CH:20]=[CH:21][C:22]([C:27]([F:30])([F:28])[F:29])=[C:23]([CH:26]=2)[C:24]#[N:25])=[CH:16][CH:15]=1)[CH2:3][OH:4]

Participants

Reactant 2

HCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

HCID 54767676HCID 54767676, compound

Product 1

HCID 54767677HCID 54767677, compound

Procedure

Compound 141 (white solid) was prepared following the procedure described for preparing compound 139 using Ad-mix-α instead of Ad-mix-β: 1H-NMR (400 MHz, CD3OD): δ 7.82 (d, 1H, 8.8 Hz), 7.53-7.57 (m, 3H), 7.34-7.39 (m, 2H), 7.31 (s, 1H), 7.23-7.27 (m, 3H), 7.1-7.14 (m, 1H), 5.44-5.51 (m, 1H), 3.89-3.95 (m, 1H), 3.72-3.76 (m, 1H), 3.47-3.63 (m, 3H), 3.12-3.18 (m, 1H), 2.86-2.97 (m, 1H); LC/MS: m/z=535.2 [M+Na]+ (Calc: 512.5).

Sources & evidence

ORD record: ord-24740d4362b74ba189f3ab123fa93dad
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212139B2

Reaction notes

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