Stannous chloride dihydrate → HCID 71486776, compound

HRID 627798Notes

Reaction equation

HRID 627798 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]3[C:21]([N:22]4[CH2:30][C:29]5[C:24](=[C:25]([N+:31]([O-])=O)[CH:26]=[CH:27][CH:28]=5)[C:23]4=[O:34])=[CH:20][N:19](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[C:16]3=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>CCO.C(Cl)Cl>[NH2:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]2[C:24]=1[C:23](=[O:34])[N:22]([C:21]1[C:15]3[C:16](=[N:17][CH:18]=[C:13]([C:10]4[CH:11]=[CH:12][C:7]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])=[CH:8][CH:9]=4)[N:14]=3)[NH:19][CH:20]=1)[CH2:30]2

Participants

6

Reactant 3

HCID 61436Stannous chloride dihydrate2×HCID 516892Sodium BicarbonateHCID 71143579HCID 71143579, compound

Product 1

HCID 71486776HCID 71486776, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

2-[2-(4-isopropylsulfonylphenyl)-5-trityl-pyrrolo[2,3-b]pyrazin-7-yl]-7-nitro-isoindolin-1-one (148 mg, 0.2056 mmol) suspended in EtOH (5 mL) and mixture heated to 70° C. SnCl2.2H2O (232.0 mg, 1.028 mmol) added and the mixture heated at reflux. After 1 h a further ˜200 mg SnCl2.2H2O added. After 1 h reaction mixture cooled, diluted with DCM and sat NaHCO3 added. Mixture stirred vigorously for 30 mins then passed through a phase separator cartridge. Org phase concentrated to a yellow solid (158 mg). This material deprotected using Method E Step 2 to give the title compound after purification using hplc; 1H NMR (400 MHz, DMSO) δ 1.21 (6H, d), 3.49 (1H, sep), 5.35 (2H, s), 6.22 (2H, s), 6.65 (1H, d), 6.81 (1H, d), 7.31 (1H, dd), 7.99 (2H, d), 8.43 (1H, s), 8.50 (2H, d), 9.07 (1H, s), 12.27 (1H, brs) ppm; MS (ES+) 448.0.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux
  3. customAfter 1 h reaction mixture
  4. temperaturecooled
  5. additionadded
  6. concentrationOrg phase concentrated to a yellow solid (158 mg)

Sources & evidence

ORD record
ord-d14820b4294e451fbb13bc9df32bb54e
Source dataset
uspto-grants-2016_04
Patent number
US09309250B2

Reaction notes

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