Hydrochloric Acid → HCID 59468406, compound

HRID 1012184Notes

Reaction equation

HRID 1012184 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-pyrimdin-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) δ 2.15 (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-e389718458b24e7a932573f4debde9b0
Source dataset
uspto-grants-2011_07
Patent number
US07977481B2

Reaction notes

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