Hydrochloric Acid → HCID 69566254, compound

HRID 2354162Notes

Reaction equation

HRID 2354162 reaction equation
C([O:5][C:6](=[O:38])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[N:20]=[CH:19][N:18]([C:24]2[CH:29]=[C:28]([C:30]([NH:32][CH:33]4[CH2:35][CH2:34]4)=[O:31])[CH:27]=[CH:26][C:25]=2[CH3:36])[C:17]3=[O:37])[CH2:10][CH2:9]1)(C)(C)C.Cl.O>C(Cl)Cl.O1CCOCC1>[CH:33]1([NH:32][C:30]([C:28]2[CH:27]=[CH:26][C:25]([CH3:36])=[C:24]([N:18]3[C:17](=[O:37])[C:16]4[C:21](=[CH:22][CH:23]=[C:14]([N:11]5[CH2:10][CH2:9][N:8]([CH2:7][C:6]([OH:38])=[O:5])[CH2:13][CH2:12]5)[CH:15]=4)[N:20]=[CH:19]3)[CH:29]=2)=[O:31])[CH2:34][CH2:35]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 69582132HCID 69582132, compound

Product 1

HCID 69566254HCID 69566254, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl-[4-(3-{5-[(cyclopropylamino)carbonyl]-2-methylphenyl}-4-oxo-3,4-dihydroquinazolin-6-yl)piperazin-1-yl]acetate (0.28 g) in methylene chloride (10 ml) was added 4N HCl in dioxane (3 ml). After 72 hours water (15 ml) was added and the solution poured onto an ion exchange column (isolute SCX-2 column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK). The column was washed with water (2×50 ml), methanol (2×50 ml) and the product eluted with 2N ammonia in methanol. The fractions containing product were evaporated in vacuo, triuration with iso-hexane/ethyl acetate gave the title compound (0.21 g); NMR Spectrum: (DMSOd6) 0.61 (m, 4H), 2.12 (s, 3H), 2.70 (m, 4H), 2.84 (m, 1H), 3.09 (s, 2H), 3.28 (m, 4H), 7.49 (m, 2H), 7.62 (m, 2H), 7.81 (d, 1H), 7.89 (m, 1H), 8.07 (s, 1H), 8.44 (d, 1H); Mass Spectrum: M+H+ 462.

Workup

  1. additionthe solution poured onto an ion exchange column (isolute SCX-2 column from International Sorbent Technology Limited, Henoed, Mid-Glamorgan, UK)
  2. washThe column was washed with water (2×50 ml), methanol (2×50 ml)
  3. washthe product eluted with 2N ammonia in methanol
  4. additionThe fractions containing product
  5. customwere evaporated in vacuo, triuration with iso-hexane/ethyl acetate

Sources & evidence

ORD record
ord-a924ecc0e3d84af09aab86f80e3f8ecd
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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