Hydrochloric Acid → HCID 86603906, compound

HRID 2217134Notes

Reaction equation

HRID 2217134 reaction equation
[ClH:1].[P:2]([O:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([NH:35][C:36]3[S:37][C:38]([CH2:41][C:42]([NH:44][C:45]4[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=4)=[O:43])=[CH:39][N:40]=3)=[N:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:52][CH3:53])([O:9]C(C)(C)C)([O:4]C(C)(C)C)=[O:3]>O1CCOCC1>[ClH:1].[ClH:1].[P:2]([OH:4])([OH:9])([O:14][CH2:15][C@@H:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([NH:35][C:36]3[S:37][C:38]([CH2:41][C:42]([NH:44][C:45]4[CH:50]=[CH:49][CH:48]=[C:47]([F:51])[CH:46]=4)=[O:43])=[CH:39][N:40]=3)=[N:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:52][CH3:53])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86603907HCID 86603907, compound

Product 1

HCID 86603906HCID 86603906, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrochloric acid (10.4 ml of a 4.0 N solution in 1,4-dioxane, 41.5 mmol) was added, dropwise to a solution of di(tert-butyl) ((2S)-1-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl phosphate (4.49 g, 5.92 mmol) in 1,4-dioxane (180 ml) upon which a light yellow solid precipitated from the reaction mixture. The resulting heterogeneous reaction mixture was stirred for a further 20 hours before the precipitate was collected, washed with 1,4-dioxane (80 ml) and acetonitrile (2×100 ml) and dried in vacuo to yield ((2S)-1-(3-((4-((5-(2-((3-fluorophenyl)amino)-2-oxoethyl)-1,3-thiazol-2-yl)amino)-6-methoxyquinazolin-7-yl)oxy)propyl)pyrrolidin-2-yl)methyl dihydrogen phosphate bis-hydrochloride as a light yellow solid (4.40 g, 97% yield):

Workup

  1. customprecipitated from the reaction mixture
  2. customwas collected
  3. washwashed with 1,4-dioxane (80 ml) and acetonitrile (2×100 ml)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-eab434c8380546f08ada6c7f4365bc44
Source dataset
uspto-grants-2008_08
Patent number
US07407946B2

Reaction notes

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