Pyridine → HCID 117777637, compound

HRID 64196Notes

Reaction equation

HRID 64196 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:32]=[CH:31][C:9]3[N:10]([C:13]4[CH:14]=[C:15]([NH:27][C:28](=[O:30])[CH3:29])[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.[CH:39]1([S:42](Cl)(=[O:44])=[O:43])[CH2:41][CH2:40]1>C(Cl)Cl>[CH:39]1([S:42]([N:1]2[CH:5]=[C:4]([C:6]3[CH:32]=[CH:31][C:9]4[N:10]([C:13]5[CH:14]=[C:15]([NH:27][C:28](=[O:30])[CH3:29])[CH:16]=[C:17]([C:19]6[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=6[F:26])[CH:18]=5)[CH:11]=[N:12][C:8]=4[CH:7]=3)[CH:3]=[N:2]2)(=[O:44])=[O:43])[CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 2760919Cyclopropanesulfonyl chlorideHCID 117777562HCID 117777562, compound

Product 1

HCID 117777637HCID 117777637, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 326 (50 mg, 0.116 mmol) in DCM was added pyridine (0.5 ml) followed by cyclopropanesulfonyl chloride (20 mg, 0.139 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 90% yield (42 mg). 1H NMR (400 MHz, CD3OD): δ 8.58 (s, 1H), 8.52 (s, 1H), 8.33 (s, 1H), 8.09 (s, 1H), 8.05 (s, 1H), 7.74-7.62 (m, 4H), 7.49 (s, 1H), 7.17-7.08 (m, 2H), 3.0 (m, 1H), 2.2 (s, 3H), 1.1 (d, 4H); LC-MS (ESI): Calculated mass: 533.5; Observed mass: 534.1 [M+H]+ (rt: 1.61 min).

Workup

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

Sources & evidence

ORD record
ord-4f9072f5e253431c8a70dfe738526496
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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