Hydrochloric Acid → HCID 59471880, compound

HRID 2204894Notes

Reaction equation

HRID 2204894 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:21]2[O:25][C:24]([C:26]3[CH:31]=[CH:30][C:29]([C@H:32]([NH:37]S(C(C)(C)C)=O)[C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=3)=[N:23][N:22]=2)=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH:18]([CH3:20])[CH3:19])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:7][N:8]=1>CO>[NH2:37][C@@H:32]([C:29]1[CH:30]=[CH:31][C:26]([C:24]2[O:25][C:21]([C:4]3[C:3]([NH2:2])=[N:8][CH:7]=[C:6]([C:9]4[CH:14]=[CH:13][C:12]([S:15]([CH:18]([CH3:19])[CH3:20])(=[O:17])=[O:16])=[CH:11][CH:10]=4)[N:5]=3)=[N:22][N:23]=2)=[CH:27][CH:28]=1)[C:33]([F:34])([F:35])[F:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59472402HCID 59472402, compound

Product 1

HCID 59471880HCID 59471880, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

HCl (35.27 μL of 3 M, 0.1058 mmol) was added to a solution of N-[(1S)-1-[4-[5-[3-amino-6-(4-isopropylsulfonylphenyl)pyrazin-2-yl]-1,3,4-oxadiazol-2-yl]phenyl]-2,2,2-trifluoro-ethyl]-2-methyl-propane-2-sulfinamide (253.3 mg, 0.05288 mmol) in MeOH (1 mL) and the resulting solution stirred at room temperature overnight. The reaction mixture was concentrated to dryness under reduced pressure and the residue triturated with acetonitrile and filtered. The solid was taken up in a mixture of acetonitrile/water/MeOH and passed through the bicarbonate cartridge. The eluent was concentrated in vacuo and then triturated with acetonitrile to give the product as a yellow solid (26 mg, 99% yield); 1H NMR (400.0 MHz, DMSO) d 1.20 (d, 6H), 2.68 (d, 2H), 3.41-3.51 (m, 1H), 4.65-4.75 (m, 1H), 7.81 (d, 2H), 7.98 (d, 2H), 8.20 (d, 2H), 8.41 (d, 2H) and 9.08 (s, 1H) ppm; MS (ES+) 519.1

Workup

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customthe residue triturated with acetonitrile
  3. filtrationfiltered
  4. additionThe solid was taken up in a mixture of acetonitrile/water/MeOH
  5. concentrationThe eluent was concentrated in vacuo
  6. customtriturated with acetonitrile

Sources & evidence

ORD record
ord-c7b8464abe594072a0e7c7034e67869e
Source dataset
uspto-grants-2016_06
Patent number
US09365557B2

Reaction notes

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