Hydrochloric Acid → HCID 10461881, compound

HRID 2217138Notes

Reaction equation

HRID 2217138 reaction equation
[P:1]([O:13][CH2:14][C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[S:36][C:37]([CH2:40][C:41]([NH:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[F:50])=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:51][CH3:52])([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].Cl.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>O1CCOCC1>[P:1]([OH:3])([OH:8])([O:13][CH2:14][C@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28]([NH:34][C:35]3[S:36][C:37]([CH2:40][C:41]([NH:43][C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=4[F:50])=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:51][CH3:52])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86603912HCID 86603912, compound

Product 1

HCID 10461881HCID 10461881, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Di(tert-butyl) ((2R)-1-(3-((4-((5-(2-((2-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl phosphate (310 mg, 0.41 mmol) in 1,4-dioxane (25 ml) was treated with 4.0 N hydrochloric acid in 1,4-dioxane (0.7 ml, 2.86 mmol) at 20° C. for 18 hours. The solid product was collected by suction filtration and washed successively with 1,4-dioxane (50 ml), acetonitrile (50 ml) then diethyl ether (50 ml), dried in vacuo to give the title compound (287 mg, 97% yield) as a yellow dihydrochloride salt:

Workup

  1. filtrationThe solid product was collected by suction filtration
  2. washwashed successively with 1,4-dioxane (50 ml), acetonitrile (50 ml)
  3. dry with materialdiethyl ether (50 ml), dried in vacuo

Sources & evidence

ORD record
ord-715aa87be72e4c759b7b0cb8ec5944f6
Source dataset
uspto-grants-2008_08
Patent number
US07407946B2

Reaction notes

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