Methanesulfonamide → HCID 86703703, compound

HRID 1849818Notes

Reaction equation

C(C1(COC2C(C3CC3)=CC(C(O)=O)=C(F)C=2)C2CC3CC(CC1C3)C2)#N.[CH:28]1([C:31]2[C:32]([O:41][CH:42]3[CH2:47][CH2:46][C:45]4([CH2:52][CH2:51][CH2:50][CH2:49][CH2:48]4)[CH2:44][CH2:43]3)=[CH:33][C:34]([F:40])=[C:35]([CH:39]=2)[C:36]([OH:38])=O)[CH2:30][CH2:29]1.CS(N)(=O)=O.[N:58]1([S:62]([NH2:65])(=[O:64])=[O:63])[CH2:61][CH2:60][CH2:59]1>>[N:58]1([S:62]([NH:65][C:36](=[O:38])[C:35]2[CH:39]=[C:31]([CH:28]3[CH2:30][CH2:29]3)[C:32]([O:41][CH:42]3[CH2:47][CH2:46][C:45]4([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52]4)[CH2:44][CH2:43]3)=[CH:33][C:34]=2[F:40])(=[O:64])=[O:63])[CH2:61][CH2:60][CH2:59]1

Participants

Reactant 4

HCID 72879Methanesulfonamide

HCID 450805661-Azetidinesulfonamide

HCID 867036554-((2-Cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid

HCID 86703704HCID 86703704, compound

Product 1

HCID 86703703HCID 86703703, compound

Procedure

Following the procedure as described in Example 332 Step 7 and making non-critical variations to replace 4-((2-cyanoadamantan-2-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid with 5-cyclopropyl-2-fluoro-4-(spiro[5.5]undecan-3-yloxy)benzoic acid and making variations as required to replace methanesulfonamide with azetidine-1-sulfonamide, the title compound was obtained as a white solid (0.045 g, 44%): 1H NMR (300 MHz, DMSO-d6) δ11.57 (s, 1H), 7.13 (d, J=8.5 Hz, 1H), 7.00 (d, J=13.3 Hz, 1H), 4.62-4.54 (m, 1H), 4.04 (t, J=7.8 Hz, 4H), 2.74-2.55 (m, 2H), 2.29-1.97 (m, 2H), 1.84-1.73 (m, 2H), 1.69-1.51 (m, 4H), 1.38-1.23 (m, 11H), 0.90-0.86 (m, 2H), 0.70-0.65 (m, 2H); MS (ES+) m/z 465.1 (M+1).

Sources & evidence

ORD record: ord-c921be6ab1b74c5b8b448f07b2e6f11b
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952169B2

Reaction notes

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