Methanesulfonamide → HCID 86703584, compound

HRID 1849710Notes

Reaction equation

HRID 1849710 reaction equation
C12(COC3C(C4CC4)=CC(C(O)=O)=CN=3)CC3CC(CC(C3)C1)C2.[Cl:25][C:26]1[C:27]([O:35][CH2:36][C:37]23[CH2:47][C:41]4([F:48])[CH2:42][C:43]([F:46])([CH2:45][C:39]([F:49])([CH2:40]4)[CH2:38]2)[CH2:44]3)=[N:28][CH:29]=[C:30]([CH:34]=1)[C:31]([OH:33])=O.COC[CH2:53][S:54]([NH2:57])(=[O:56])=[O:55].CS(N)(=O)=O>>[Cl:25][C:26]1[C:27]([O:35][CH2:36][C:37]23[CH2:38][C:39]4([F:49])[CH2:45][C:43]([F:46])([CH2:42][C:41]([F:48])([CH2:40]4)[CH2:47]2)[CH2:44]3)=[N:28][CH:29]=[C:30]([CH:34]=1)[C:31]([NH:57][S:54]([CH3:53])(=[O:56])=[O:55])=[O:33]

Participants

5

Reactant 4

HCID 72879MethanesulfonamideHCID 189515062-Methoxyethane-1-sulfonamideHCID 867029246-(Adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acidHCID 86703585HCID 86703585, compound

Product 1

HCID 86703584HCID 86703584, compound

Procedure

Following the procedure as described in Example 271 and making variations as required to replace 6-(adamantan-1-ylmethoxy)-5-cyclopropylnicotinic acid with 5-chloro-6-((3,5,7-trifluoroadamantan-1-yl)methoxy)nicotinic acid and to replace 2-methoxyethane- sulfonamide with methyl sulfonamide. Purification by reverse phase HPLC, the title compound was obtained as a colorless solid (0.13 g, 18%): 1H NMR (300 MHz, DMSO-d6) δ 12.24 (br s, 1H), 8.63 (d, J=2.2 Hz, 1H), 8.36 (d, J=2.2 Hz, 1H), 4.29 (s, 2H), 3.33 (s, 3H), 2.24-2.14 (m, 3H), 2.06-1.96 (m, 3H), 1.81-1.74 (m, 6H); MS (ES−) m/z 451.2, 453.2 (M−1).

Workup

  1. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-f9a884ec859e456788f07cf275919d1e
Source dataset
uspto-grants-2015_02
Patent number
US08952169B2

Reaction notes

Loading…