Stannous chloride dihydrate → HCID 11292979, compound

HRID 1294630Notes

Reaction equation

HRID 1294630 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1)([O-])=O.O.O.Cl[Sn]Cl>CCOC(C)=O.C(Cl)Cl>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:23]([N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)=[O:24])=[C:8]([NH:10][S:11]([C:14]2[C:19]3=[N:20][S:21][N:22]=[C:18]3[CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 11316813HCID 11316813, compound

Product 1

HCID 11292979HCID 11292979, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A solution of benzo[1,2,5]thiadiazole-4-sulfonic acid [5-nitro-2-(piperidine-1-carbonyl)-phenyl]-amide (EXAMPLE 2; 90 mg, 2.0 mmol) was dissolved in 1:1 EtOAc/DCM (10 mL), and SnCl2.2H2O (2.3 g, 10 mmol) was added. The mixture was stirred overnight at ambient temperature then concentrated in vacuo. The resulting oil was suspended in DCM and neutralized by shaking with aqueous NaHCO3. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (69 mg, 1.7 mmol, 82%). TLC (silica gel, 3:1 EtOAc/hexanes): Rf=0.42. MS (ESI): m/z 418 [M+H]+, 440 [M+Na]+. HPLC (reversed-phase): RT=8.15 min (single peak). 1H NMR (400 MHz, CDCl3): (rotameric broadening) 9.80 (s, 1H), 8.40 (dd, J=8.8 Hz, 1.0 Hz, 1H); 8.15 (dd; J=7.0 Hz, 1.0 Hz, 1H), 7.82 (dd, J=8.8 Hz, 1.0 Hz, 1H), 6.77 (d, J=8.4 Hz, 1H), 6.74 (d, J=2.2 Hz, 1H), 6.19 (dd, J=8.4 Hz, 2.3 Hz, 1H), 5.75 (d, J=2.3 Hz, 2H), 2.96 (bs, 4H), 1.45 (bs, 2H), 1.24 (bs, 4H).

Workup

  1. additionwas added
  2. concentrationthen concentrated in vacuo
  3. stirringneutralized by shaking with aqueous NaHCO3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d278cd5a7c049618bda0b4d0611a8a3
Source dataset
uspto-grants-2007_07
Patent number
US07241759B2

Reaction notes

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