Hydrochloric Acid → Hydrochloric Acid

HRID 1508678Notes

Reaction equation

HRID 1508678 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:26])=[CH:20][CH:19]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[OH:27]S(O)(=O)=O.C([O-])(O)=O.[Na+].[ClH:37]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]3[CH2:14][CH2:15][CH2:16][C:11]3=[C:10]([NH:17][C:18]3[CH:19]=[CH:20][C:21]([CH2:24][C:25]([NH2:26])=[O:27])=[CH:22][CH:23]=3)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[ClH:37]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 742208442-[4-[[2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenyl]acetonitrile

Product 2

HCID 313Hydrochloric AcidYield 19%HCID 742209062-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)amino)phenyl)acetamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

An 18 mL-vial was charged with 2-[4-[[2-(3-Chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenyl]acetonitrile (12 mg, 0.033 mmol, synthesis of this compound was described in EXAMPLE 1). Concentrated H2SO4 (0.5 ml) was added at 0° C. The mixture was standing at room temperature for 6 hr. And then the mixture was added very slowly to NaHCO3 aq. at 0° C. The precipitate was collected and washed with water, dried. The product thus obtained was treated with 4N HCl in dioxane and the volatile material was removed under reduced pressure to give the desired product 2-[4-[[2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl]amino]phenyl]acetamide as HCl salt (2.6 mg, 19% yield). MW=377.87. 1H NMR (CDCl3, 360 MHz) δ 7.83 (s, 1H), 7.69 (m, 1H), 7.18-7.30 (m, 7H), 5.77 (brs, 1H), 5.44 (brs, 2H), 3.58 (s, 2H), 3.08 (t, J=7.70 Hz, 2H), 2.83 (t, J=7.10 Hz, 2H), 2.21 (m, 2H).

Workup

  1. custom12 mg, 0.033 mmol, synthesis of this compound
  2. customThe precipitate was collected
  3. washwashed with water
  4. customdried
  5. customThe product thus obtained
  6. customthe volatile material was removed under reduced pressure

Sources & evidence

ORD record
ord-db737308fc1f4931a77ca4a2c211c93e
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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