Hydrochloric Acid → HCID 86603910, compound

HRID 2217137Notes

Reaction equation

HRID 2217137 reaction equation
[ClH:1].[P:2]([O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:35]=[C:34]3[C:29]([C:30]([NH:36][C:37]4[S:38][C:39]([CH2:42][C:43]([NH:45][C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=5[F:52])=[O:44])=[CH:40][N:41]=4)=[N:31][CH:32]=[N:33]3)=[CH:28][C:27]=2[O:53][CH3:54])[CH2:18][CH2:17]1)([O:9]C(C)(C)C)([O:4]C(C)(C)C)=[O:3]>O1CCOCC1>[ClH:1].[ClH:1].[P:2]([OH:9])([OH:4])([O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][O:25][C:26]2[CH:35]=[C:34]3[C:29]([C:30]([NH:36][C:37]4[S:38][C:39]([CH2:42][C:43]([NH:45][C:46]5[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=5[F:52])=[O:44])=[CH:40][N:41]=4)=[N:31][CH:32]=[N:33]3)=[CH:28][C:27]=2[O:53][CH3:54])[CH2:18][CH2:17]1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86603911HCID 86603911, compound

Product 1

HCID 86603910HCID 86603910, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrochloric acid (1 ml of a 4.0 N solution in 1,4-dioxane, 4 mmol) was added, dropwise to a solution of di(tert-butyl) (1-(3-((4-((5-(2-((2-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)piperidin-4-yl)methyl phosphate (assumed 379 mg, 0.49 mmol) in 1,4-dioxane (15 ml) upon which a light yellow solid precipitated from the reaction mixture. The resulting heterogeneous reaction mixture was stirred for a further 20 hours and the precipitate was filtered and washed with 1,4-dioxane (2×5 ml) then dried under high vacuum for 48 hours to furnish (1-(3-((4-((5-(2-((2-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)piperidin-4-yl)methyl dihydrogen phosphate bis-hydrochloride as a light yellow solid (302 mg, 84% yield):

Workup

  1. customprecipitated from the reaction mixture
  2. filtrationthe precipitate was filtered
  3. washwashed with 1,4-dioxane (2×5 ml)
  4. customthen dried under high vacuum for 48 hours

Sources & evidence

ORD record
ord-88731302a63f4717bbb79d29b7a6cc6b
Source dataset
uspto-grants-2008_08
Patent number
US07407946B2

Reaction notes

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