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 71572097, compound

HRID 2276802Notes

Reaction equation

HRID 2276802 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:18]=[C:17]([C:19]([NH2:21])=[O:20])[CH:16]=[C:15]([C@@H:22]([OH:25])[CH2:23][OH:24])[N:14]=3)=[CH:9][CH:8]=2)=[C:4]([F:28])[CH:3]=1.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>>[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:18]=[C:17]([C:19]([NH2:21])=[O:20])[CH:16]=[C:15]([C@H:22]([OH:25])[CH2:23][OH:24])[N:14]=3)=[CH:11][CH:12]=2)=[C:4]([F:28])[CH:3]=1

Participants

3

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)phthalazineHCID 71525317HCID 71525317, compound

Product 1

HCID 71572097HCID 71572097, compound

Procedure

(S)-2-(4-(4-chloro-2-fluorophenoxy)phenyl)-6-(1,2-dihydroxyethyl)pyrimidine-4-carboxamide (Compound Example No. 10) was prepared in a similar fashion to (R)-2-(4-(4-chloro-2-fluorophenoxy)phenyl)-6-(1,2-dihydroxyethyl)pyrimidine-4-carboxamide (Compound Example No. 9) using AD-mix-α instead of AD-Mix-β. 1H NMR (400 MHz, CD3OD): 8.49 (2H, d, J=8.8 Hz), 8.03 (1H, s), 7.30 (1H, dd, J=2.4, 10 Hz), 7.18-7.10 (2H, m), 6.96 (2H, d, J=9.2 Hz), 4.73 (1H, dd, J=3.6, 6.4 Hz), 3.89 (1H, dd, J=3.6, 11 Hz), 3.75 (1H, dd, J=6.0, 11 Hz); LC/MS: m/z=404[M+H]+.

Sources & evidence

ORD record
ord-33ffa90d49bb420d8fb5040c014824e8
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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