Hydrochloric Acid → HCID 9986889, compound

HRID 2217140Notes

Reaction equation

HRID 2217140 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]=[C:46]([F:50])[C:45]=4[F:51])=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:52][CH3:53])([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]=[C:46]([F:50])[C:45]=4[F:51])=[O:42])=[CH:38][N:39]=3)=[N:29][CH:30]=[N:31]2)=[CH:26][C:25]=1[O:52][CH3:53])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 86603913HCID 86603913, compound

Product 1

HCID 9986889HCID 9986889, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Di(tert-butyl) ((2R)-1-(3-((4-((5-(2-((2,3-difluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl phosphate (230 mg, 0.296 mmol) in 1,4-dioxane (15 ml) was treated with 4.0 N hydrochloric acid in 1,4-dioxane (0.9 ml, 3.43 mmol) at 20° C. for 18 hours. The solid product was collected by suction filtration, washed with i) 1,4-dioxane (50 ml), ii) acetonitrile (50 ml) and iii) diethyl ether (50 ml) and then dried in vacuo to yield the title compound (166 mg, 72% yield) as a yellow dihydrochloride salt:

Workup

  1. filtrationThe solid product was collected by suction filtration
  2. washwashed with i) 1,4-dioxane (50 ml), ii) acetonitrile (50 ml) and iii) diethyl ether (50 ml)
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b157a0dcc6e24eb187ee81e44af19356
Source dataset
uspto-grants-2008_08
Patent number
US07407946B2

Reaction notes

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