HCID 86703581, compound → HCID 86703589, compound

HRID 1849714Notes

Reaction equation

N1(S(N[C:9](=O)[C:10]2[CH:15]=C(Cl)C(OCC34CC5CC(CC(CO)(C5)C3)C4)=CC=2F)(=O)=O)CCC1.[C@@H:33]12[CH2:39][C@@H:36]([CH2:37][CH2:38]1)[CH2:35][C@@H:34]2[O:40][C:41]1[C:53](Cl)=[CH:52][C:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[C:43]([F:55])[CH:42]=1>>[C@@H:33]12[CH2:39][C@@H:36]([CH2:37][CH2:38]1)[CH2:35][C@@H:34]2[O:40][C:41]1[C:53]([CH:15]2[CH2:10][CH2:9]2)=[CH:52][C:44]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[C:43]([F:55])[CH:42]=1

Participants

Reactant 2

HCID 86703581HCID 86703581, compound

HCID 86703588HCID 86703588, compound

Product 1

HCID 86703589HCID 86703589, compound

Procedure

Following the procedure as described in Example 278 step 7 and making variations as required to replace N-(azetidin-1-ylsulfonyl)-5-chloro-2-fluoro-4-((3-(hydroxymethyl)-adamantan-1-yl)methoxy)benzamide with tert-Butyl 4-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-yloxy)-5-chloro-2-fluorobenzoate. Purification by silica gel column chromatography (10:1 hexanes:ethyl acetate) gave the title compound as a colorless oil (0.77 g, quant): 1H NMR (300 MHz, CDCl3) δ 7.33 (d, J=8.3 Hz, 1H), 6.45 (d, J=13.0 Hz, 1H), 4.20-4.13 (m, 1H), 2.49-2.44 (m, 1H), 2.35-2.29 (m, 1H), 2.01-1.91 (m, 1H), 1.82-1.73 (m, 1H), 1.70-1.63 (m, 1H), 1.61-1.56 (m, 1H), 1.55 (s, 9H), 1.50-1.44 (m, 1H), 1.27-1.09 (m, 4H), 0.88-0.81 (m, 2H), 0.63-0.56 (m, 2H); MS (ES+) m/z 291.2 (M-55).

Workup

customPurification by silica gel column chromatography (10:1 hexanes:ethyl acetate)

Sources & evidence

ORD record: ord-c6b53543260c458abdde16892b41c709
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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