Hydrochloric Acid → HCID 59468406, compound

HRID 1716399Notes

Reaction equation

HRID 1716399 reaction equation
C(OC(=O)[N:7]([CH2:27][C:28](=[O:30])[CH3:29])[C:8]1[S:9][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH3:26])[CH:23]=[CH:24][CH:25]=3)[N:14]=2)=[CH:11][CH:12]=1)(C)(C)C.Cl>O1CCOCC1>[C:22]1([CH3:26])[CH:23]=[CH:24][CH:25]=[C:20]([NH:19][C:15]2[N:14]=[C:13]([C:10]3[S:9][C:8]([NH:7][CH2:27][C:28](=[O:30])[CH3:29])=[CH:12][CH:11]=3)[CH:18]=[CH:17][N:16]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59468431HCID 59468431, compound

Product 1

HCID 59468406HCID 59468406, compoundYield 10.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(2-Oxo-propyl)-[5-(2-m-tolylamino-pyrimidin-4-yl)-thiophen-2-yl]-carbamic acid tert-butyl ester (0.078 mmol) was treated with 1 mL 4N HCl in dioxane. After 1½ hours, the mixture was concentrated in vacuo and redissolved in EtOAc. The organics were washed with saturated NaHCO3, dried over Na2SO4 and concentrated. The residue was purified by prep LCMS to afford title compound (2.8 mg, 10.5% yield for 2 steps). %). MS: m/z 339 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ2.15 (s, 3H), 2.318 (s, 3H), 4.077 (d, J=5.5 Hz, 2H), 5.94 (d, J=4 Hz, 1H), 6.73 (d, J=8 Hz, 1H), 7.02 (d, J=5.5 Hz, 1H), 7.13 (t, J=8 Hz, 1H), 7.41 (t, J=6 Hz, 1H), 7.52 (br d, J=9 Hz, 1H), 7.59 (d, J=4 Hz, 1H), 7.75 (br s, 1H), 8.19 (d, J=5.5 Hz, 1H), 9.27 (s, 1H).

Workup

  1. waitAfter 1½ hours
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionredissolved in EtOAc
  4. washThe organics were washed with saturated NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by prep LCMS

Sources & evidence

ORD record
ord-7344d269100b4dcdb7741b0215ceee2b
Source dataset
uspto-grants-2010_09
Patent number
US07803806B2

Reaction notes

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