Hydrochloric Acid → HCID 58724181, compound

HRID 2356224Notes

Reaction equation

HRID 2356224 reaction equation
[CH3:1][N:2]([CH3:23])[C@@H:3]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[N:16](C(=O)C)[CH2:15][CH2:14]3)(=[O:10])=[O:9])[CH2:4]1.Cl>C1COCC1>[NH:16]1[C:17]2[C:13](=[CH:12][C:11]([S:8]([N:5]3[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:23])[CH3:1])[CH2:4]3)(=[O:10])=[O:9])=[CH:19][CH:18]=2)[CH2:14][CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58724142HCID 58724142, compound

Product 1

HCID 58724181HCID 58724181, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

(R)-1-(5-(3-(dimethylamino)pyrrolidin-1-ylsulfonyl)indolin-1-yl)ethanone was dissolved in THF. A 2 N HCl solution of equal volume was added, and the reaction mixture was stirred at 60° C. for 1 h. Volatiles were removed in vacuo, and the product that was precipitated was collected on a fritted glass funnel, washed with water, and was dried in vacuo at 45° C. overnight to obtain the title compound in 65% yield. 1H NMR (300 MHz, MeOD) δ ppm 2.02-2.22 (m, 1 H) 2.25-2.47 (m, 1 H) 2.88 (s, 6 H) 3.14-3.26 (m, 1 H) 3.28-3.33 (m, 2 H) 3.34-3.64 (m, 4 H) 3.82-4.01 (m, 2 H) 7.51-7.60 (m, 1 H) 7.87 (d, J=8.67 Hz, 1 H) 7.93 (s, 1 H).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe product that was precipitated
  3. customwas collected on a fritted glass funnel
  4. washwashed with water
  5. customwas dried in vacuo at 45° C. overnight

Sources & evidence

ORD record
ord-2f890220b8614fe8afb75c30a8f54dbf
Source dataset
uspto-grants-2010_07
Patent number
US07759339B2

Reaction notes

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