Hydrochloric Acid → HCID 10055133, compound

HRID 2217133Notes

Reaction equation

HRID 2217133 reaction equation
[P:1]([O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:34]=[C:33]3[C:28]([C:29]([NH:35][C:36]4[S:37][C:38]([CH2:41][C:42]([NH:44][C:45]5[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=5)=[O:43])=[CH:39][N:40]=4)=[N:30][CH:31]=[N:32]3)=[CH:27][C:26]=2[O:52][CH3:53])[CH2:17][CH2:16]1)([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:8])([OH:3])([O:13][CH2:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][O:24][C:25]2[CH:34]=[C:33]3[C:28]([C:29]([NH:35][C:36]4[S:37][C:38]([CH2:41][C:42]([NH:44][C:45]5[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=5)=[O:43])=[CH:39][N:40]=4)=[N:30][CH:31]=[N:32]3)=[CH:27][C:26]=2[O:52][CH3:53])[CH2:17][CH2:16]1)=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 11520612HCID 11520612, compound

Product 1

HCID 10055133HCID 10055133, compoundYield 118.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Di(tert-butyl) (1-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)piperidin-4-yl)methyl phosphate (6.64 g, 8.6 mmol), in 1,4-dioxane (250 ml) was treated with 4.0 N hydrochloric acid in 1,4-dioxane (15 ml, 60 mmol) at 20° C. for 18 hours. The solid product was collected by suction filtration and washed with i) 1,4-dioxane (100 ml), ii) acetonitrile (100 ml) and iii) diethyl ether (100 ml), Prolonged drying in vacuo yielded the title compound (6.73 g, 98% yield) as a yellow dihydrochloride salt:

Workup

  1. filtrationThe solid product was collected by suction filtration
  2. washwashed with i) 1,4-dioxane (100 ml), ii) acetonitrile (100 ml) and iii) diethyl ether (100 ml)
  3. customProlonged drying in vacuo

Sources & evidence

ORD record
ord-2333daed4fd141fe81ab94f07059e28a
Source dataset
uspto-grants-2008_08
Patent number
US07407946B2

Reaction notes

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