Pyridine → HCID 117777656, compound

HRID 64149Notes

Reaction equation

HRID 64149 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:35]=[CH:34][C:9]3[N:10]([C:13]4[CH:14]=[C:15]([NH:27][S:28]([CH:31]5[CH2:33][CH2:32]5)(=[O:30])=[O:29])[CH:16]=[C:17]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=5[F:26])[CH:18]=4)[CH:11]=[N:12][C:8]=3[CH:7]=2)[CH:3]=[N:2]1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[C:17]1[CH:18]=[C:13]([N:10]2[C:9]3[CH:34]=[CH:35][C:6]([C:4]4[CH:5]=[N:1][N:2]([S:43]([CH3:42])(=[O:45])=[O:44])[CH:3]=4)=[CH:7][C:8]=3[N:12]=[CH:11]2)[CH:14]=[C:15]([NH:27][S:28]([CH:31]2[CH2:32][CH2:33]2)(=[O:29])=[O:30])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 117777927HCID 117777927, compound

Product 1

HCID 117777656HCID 117777656, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 203 (50 mg, 0.101 mmol) in DCM was added pyridine (16 mg, 0.202 mmol, 2.0 eq.) followed by methanesulfonyl chloride (14 mg, 0.122 mmol, 1.2 eq.). The mixture was stirred for 1 h and quenched and extracted as in Example 2(b). The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to give the product in 60% yield (40 mg). H-NMR (400 MHz, DMSO-D6) δ=10.32 (s, 1H), 8.95 (s, 1H), 8.90 (s, 1H), 8.62 (s, 1H), 8.29 (s, 1H), 7.88 (d, 1H), 7.76 (dd, 2H), 7.63 (d, 2H), 7.52 (s, 1H), 7.50-7.47 (m, 1H), 7.30-7.29 (dt, 1H), 3.61 (s, 3H), 2.90-2.86 (m, 1H), 1.04-1.02 (d, 4H); LC-MS (ESI): Calculated mass: 569.6; Observed mass: 569.9 [M+H]+ (rt: 0.64 min).

Workup

  1. customquenched
  2. extractionextracted as in Example 2(b)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d28594cbda874ae8835a3cee1fe06032
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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