Hydrochloric Acid → HCID 118906762, compound

HRID 919606Notes

Reaction equation

HRID 919606 reaction equation
[S:1]([N:11]1[C:15]2[N:16]=[CH:17][N:18]=[C:19]([NH:20][CH:21]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23](C(OCCCC)=O)[CH2:22]3)[C:14]=2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].Cl>O1CCOCC1>[NH:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:21]([NH:20][C:19]2[C:14]3[CH:13]=[CH:12][N:11]([S:1]([C:4]4[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=4)(=[O:2])=[O:3])[C:15]=3[N:16]=[CH:17][N:18]=2)[CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131734884HCID 131734884, compound

Product 1

HCID 118906762HCID 118906762, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of test-butyl 3-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)azepane-1-carboxylate (1.4 g, 2.9 mmol) in 1,4-dioxane (15 mL) was added 6 N HCl (2 mL) and the reaction mixture was stirred for 2 h. The reaction mixture was concentrated in vacuo and the resultant residue was dissolved in EtOAc, washed with 10% NaHCO3. The EtOAc layer was separated, dried over Na2SO4 and concentrated in vacuo to afford the titled intermediate (910 mg, 88%), which was used in the next step without purification. LC-MS: m/z [M+1]=386.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resultant residue was dissolved in EtOAc
  3. washwashed with 10% NaHCO3
  4. customThe EtOAc layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37f870f3dffd4e12a9966d16e6662134
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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