Sodium Sulfite → HCID 53353202, compound

HRID 1478926Notes

Reaction equation

HRID 1478926 reaction equation
[CH2:1]([N:3]1[C:11]2[CH:10]=[C:9]([NH:12][C:13](=[O:24])[C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:22])=[CH2:21])=[C:16]([CH3:23])[CH:15]=3)[N:8]=[CH:7][C:6]=2[CH:5]=[CH:4]1)[CH3:2].CS(N)(=O)=[O:27].CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+].[Cl-].[Na+].[OH2:96]>O.CC(O)(C)C>[OH:96][CH2:21][C@@:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:9]2[N:8]=[CH:7][C:6]3[CH:5]=[CH:4][N:3]([CH2:1][CH3:2])[C:11]=3[CH:10]=2)=[O:24])=[CH:15][C:16]=1[CH3:23])([OH:27])[CH3:22]

Participants

8

Reactant 5

HCID 24437Sodium SulfiteHCID 72879MethanesulfonamideHCID 112172021,4-Bis(dihydroquinidine)phthalazine2×HCID 57417360Sodium chloride; waterHCID 86674849HCID 86674849, compound

Product 1

HCID 53353202HCID 53353202, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Conditions

Temperature
0 °C

Procedure

To N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-3-methyl-4-(prop-1-en-2-yl)benzamide (100 mg, 0.31 mmol) and methanesulfonamide (30 mg, 0.31 mmol) were added t-BuOH (1.6 mL). The mixture was cooled in ice bath, and then water (1.6 mL) and AD-mix-beta (550 mg, 0.39 mmol) were added to give a bi-phase orange solution. The reaction was stirred at 0° C. with slow warming to room temperature overnight. The mixture was again cooled in ice bath the next day, and a total of 500 mg of AD-mix-beta was added. No further conversion was observed after 6 hours. To the reaction mixture cooled in ice bath was added 120 mg of sodium sulfite. After being stirred for 20 min, the mixture was charged with brine (5 ml) and the mixture was extracted with EtOAc (2×5 ml). Combined organic layers were washed once with 2N KOH (5 ml) and then once with brine (5 ml). The organic layers were dried over Na2SO4, filtered, and concentrated. 1H NMR (DMSO-d6) δ: 10.47 (br. s., 1 H), 8.65 (br. s., 1 H), 8.29 (br. s., 1 H), 7.81 (d, J=8.3 Hz, 2 H), 7.56 (d, J=8.1 Hz, 1 H), 7.48 (d, J=3.3 Hz, 1 H), 6.58 (d, J=3.0 Hz, 1 H), 4.91 (s, 1 H), 4.76 (br. s., 1 H), 4.16-4.28 (m, 2 H), 3.60 (br. s., 2 H), 2.59 (s, 3 H), 1.48 (s, 3 H), 1.39 (t, J=7.2 Hz, 3 H); ESI-MS: m/z 354 (M+H)+.

Workup

  1. temperatureThe mixture was cooled in ice bath
  2. customto give a bi-phase orange solution
  3. temperaturewith slow warming to room temperature overnight
  4. temperatureThe mixture was again cooled in ice bath the next day
  5. temperatureTo the reaction mixture cooled in ice bath
  6. stirringAfter being stirred for 20 min
  7. extractionthe mixture was extracted with EtOAc (2×5 ml)
  8. washCombined organic layers were washed once with 2N KOH (5 ml)
  9. dry with materialThe organic layers were dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-b63ab71e05014c8096f782d8139c0198
Source dataset
uspto-grants-2016_08
Patent number
US09403819B2

Reaction notes

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