2-Cyclopropylethan-1-ol → 5-chloro-2-fluoro-N-(methylsulfonyl)-4-(((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)oxy)benzamide

HRID 1427804Notes

Reaction equation

C1(CCO)CC1.[CH3:7][C@H:8]1[C@H:13]([OH:14])[CH2:12][C@@H:11]2[CH2:15][C@H:9]1[C:10]2([CH3:17])[CH3:16].FC1C=C(F)C(F)=CC=1C(NS(C)(=O)=O)=O.[Cl:34][C:35]1[C:36](F)=[CH:37][C:38]([F:48])=[C:39]([CH:47]=1)[C:40]([NH:42][S:43]([CH3:46])(=[O:45])=[O:44])=[O:41]>>[Cl:34][C:35]1[C:36]([O:14][C@@H:13]2[CH2:12][C@@H:11]3[CH2:15][C@@H:9]([C:10]3([CH3:16])[CH3:17])[C@H:8]2[CH3:7])=[CH:37][C:38]([F:48])=[C:39]([CH:47]=1)[C:40]([NH:42][S:43]([CH3:46])(=[O:44])=[O:45])=[O:41]

Participants

Reactant 4

HCID 1376422-Cyclopropylethan-1-ol

HCID 10524983(-)-Isopinocampheol

HCID 580424175-chloro-2,4-difluoro-N-(methylsulfonyl)benzamide

HCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 867028315-chloro-2-fluoro-N-(methylsulfonyl)-4-(((1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yl)oxy)benzamide

Procedure

Following the procedure as described in Example 1 and making variations as required to replace 2-cyclopropylethanol with (1R,2R,3R,5S)-2,6,6-trimethylbicyclo-[3.1.1]heptan-3-ol and 2,4,5-trifluoro-N-(methylsulfonyl)benzamide with 5-chloro-2,4-difluoro-N-(methylsulfonyl)-benzamide, the title compound was obtained as a colorless solid (0.06 g, 5%): 1H NMR (300 MHz, DMSO-d6) δ 12.05 (s, 1H), 7.74 (d, J=7.5 Hz, 1H), 7.33 (d, JC-F=12.6 Hz, 1H), 4.79-4.74 (m, 1H), 3.31 (s, 3H), 2.71-2.64 (m, 1H), 2.37-2.26 (m, 2H), 1.91-1.80 (m, 2H), 1.59-1.52 (m, 1H), 1.19 (s, 3H), 1.10-1.06 (m, 4H), 0.95 (s, 3H); MS (ES−) m/z 402.1, 404.1 (M−1).

Sources & evidence

ORD record: ord-4015917ff1154393b88cd847ab59d679
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933236B2

Reaction notes

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