Pyridine → HCID 117777611, compound

HRID 64124Notes

Reaction equation

HRID 64124 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:35]=[CH:34][C:15]4[N:16]([C:19]5[CH:20]=[C:21]([NH:30][C:31](=[O:33])[CH3:32])[CH:22]=[C:23]([N:25]6[CH:29]=[CH:28][CH:27]=[N:26]6)[CH:24]=5)[CH:17]=[N:18][C:14]=4[CH:13]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1.N1C=CC=CC=1.[CH3:42][S:43](Cl)(=[O:45])=[O:44]>C(Cl)Cl>[CH3:42][S:43]([N:1]1[CH2:6][CH2:5][CH:4]([N:7]2[CH:11]=[C:10]([C:12]3[CH:35]=[CH:34][C:15]4[N:16]([C:19]5[CH:20]=[C:21]([NH:30][C:31](=[O:33])[CH3:32])[CH:22]=[C:23]([N:25]6[CH:29]=[CH:28][CH:27]=[N:26]6)[CH:24]=5)[CH:17]=[N:18][C:14]=4[CH:13]=3)[CH:9]=[N:8]2)[CH2:3][CH2:2]1)(=[O:45])=[O:44]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 117777480HCID 117777480, compound

Product 1

HCID 117777611HCID 117777611, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 128 (80 mg, 0.171 mmol) in DCM (10 ml) was added pyridine (27 mg, 0.34 mmol, 2 eq.) and methanesulfonyl chloride (19 mg, 0.171 mmol, 1 eq.). The mixture was stirred for 4 h and quenched and extracted as in Example 2(b). The solvent was distilled off and the residue was purified by preparative HPLC to give the product in 19% yield (18 mg). 1H NMR (300 MHz, DMSO-d6): δ 10.52 (s, 1H), 10.06 (s, 1H), 8.58 (d, 1H), 8.43 (s, 1H), 8.24 (s, 1H), 8.06-8.00 (m, 3H), 7.89 (s, 1H), 7.83 (d, 1H), 7.78-7.74 (m, 2H), 6.62 (t, 1H), 4.36 (m, 1H), 3.01-2.94 (m, 6H), 2.30 (s, 3H), 2.13 (s, 3H), 2.10-2.01 (m, 2H); LC-MS (ESI): Calculated mass: 544.63; Observed mass: 545.2 [M+H]+ (rt: 0.40 min).

Workup

  1. customquenched
  2. extractionextracted as in Example 2(b)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by preparative HPLC
  5. customto give the product in 19% yield (18 mg)
  6. custom545.2 [M+H]+ (rt: 0.40 min)

Sources & evidence

ORD record
ord-3d43785fc2f148619280838c19e8dadf
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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