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 71572205, compound

HRID 2276803Notes

Reaction equation

HRID 2276803 reaction equation
[OH:1][C@H:2]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([NH2:27])=[O:26])[N:6]=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][C@@H:2]([C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:13][CH:12]=2)[N:8]=[C:7]([C:25]([NH2:27])=[O:26])[N:6]=1)[CH2:3][OH:4]

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 71572206HCID 71572206, compound

Product 1

HCID 71572205HCID 71572205, compound

Procedure

(S)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)pyrimidine-2-carboxamide (Compound Example No. 21) was prepared in a similar fashion to (R)-4-(1,2-dihydroxyethyl)-6-(4-(4-fluorophenoxy)phenyl)pyrimidine-2-carboxamide (Compound Example No. 20) using AD-Mix-α instead of AD-Mix-β. 1H NMR (400 MHz, CD3OD): 8.25 (2H, d, J=8.8 Hz), 8.09 (1H, s), 7.09-6.98 (6H, m), 4.75 (1H, m), 4.10 (1H, dd, J=3.6, 12 Hz), 3.77 (1H, dd, J=5.2, 12 Hz); LC/MS: m/z=370[M+H]+.

Sources & evidence

ORD record
ord-985d6d1dc1a44e7983c0584b496552a0
Source dataset
uspto-grants-2015_09
Patent number
US09133131B2

Reaction notes

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