Sodium Bicarbonate → 2-(2-Chloro-4-iodophenyl)-5-((3aR,6aS)-5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-1,3,4-thiadiazole

HRID 579342Notes

Reaction equation

HRID 579342 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([I:13])=[CH:9][C:8]=2[Cl:14])=[N:5][N:6]=1.[CH3:15][N:16]1[CH2:23][C@@H:22]2[C@@H:18]([CH2:19][NH:20][CH2:21]2)[CH2:17]1.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[Cl:14][C:8]1[CH:9]=[C:10]([I:13])[CH:11]=[CH:12][C:7]=1[C:4]1[S:3][C:2]([N:20]2[CH2:21][C@@H:22]3[C@@H:18]([CH2:17][N:16]([CH3:15])[CH2:23]3)[CH2:19]2)=[N:6][N:5]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 12958532(3aR,6aS)-2-methyl-octahydropyrrolo[3,4-c]pyrroleHCID 867271652-Bromo-5-(2-chloro-4-iodophenyl)-1,3,4-thiadiazole

Product 1

HCID 867271642-(2-Chloro-4-iodophenyl)-5-((3aR,6aS)-5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A stirred solution of 2-bromo-5-(2-chloro-4-iodophenyl)-1,3,4-thiadiazole (600 mg, 1.49 mmol) and (3aR,6aS)-2-methyloctahydropyrrolo[3,4-c]pyrrole (377 mg, 2.99 mmol) in NMP (4 mL) was heated at 120° C. for ˜18 hours. The reaction mixture was cooled to room temperature then saturated NaHCO3(aq) (30 mL) was added. The resulting suspension was left to slurry for 1 hour before filtering under vacuum to afford the title compound as a pale brown solid which was used in the next step without further purification. LC-MS: Rt 1.06 min; MS m/z 446.8 [M]+ 1H NMR (400 MHz, DMSO-d6) δ ppm 8.03 (s, 1H), 7.77-7.86 (m, 2H), 3.71 (t, J=8.84 Hz, 2H), 3.36 (br. s., 2H), 2.97 (br. s., 2H), 2.40-2.54 (m, 4H), 2.22 (s, 3H).

Workup

  1. waitThe resulting suspension was left
  2. filtrationbefore filtering under vacuum

Sources & evidence

ORD record
ord-4dffbf4593f545419d5a72960e490fc2
Source dataset
uspto-grants-2015_05
Patent number
US09040712B2

Reaction notes

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