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 71572100, compound

HRID 2276812Notes

Reaction equation

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

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 71572099HCID 71572099, compound

Product 1

HCID 71572100HCID 71572100, compound

Procedure

(S)-2-(4-(4-cyano-3-(trifluoromethyl)phenoxy)phenyl)-6-(1,2-dihydroxyethyl) pyrimidine-4-carboxamide (Compound Example No. 13) was prepared in a similar fashion to (R)-2-(4-(4-cyano-3-(trifluoromethyl) phenoxy)phenyl)-6-(1,2-dihydroxy-ethyl)pyrimidine-4-carboxamide (Compound Example No. 12) using AD-Mix alpha instead of AD-Mix beta. 1H NMR (400 MHz, DMSO-d6) δ 8.80-8.70 (2 H, m), 8.69-8.61 (1 H, m), 8.23-8.15 (1 H, m), 8.07-8.02 (1 H, m), 8.01-7.96 (1 H, m), 7.67-7.60 (1 H, m), 7.49-7.41 (1 H, m), 7.42-7.34 (2 H, m), 5.86-5.78 (1 H, m), 4.87-4.79 (1 H, m), 4.75-4.66 (1 H, m), 3.85-3.76 (1 H, m), 3.74-3.63 (1 H, m); LC/MS: m/z=445 [M+H]+.

Sources & evidence

ORD record: ord-9d18303979144f4783e63f1ff25bd647
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133131B2

Reaction notes

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