Hydrochloric Acid → 3-(4-(2-(4-(4-Phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylamino)propyl dihydrogen phosphate dihydrochloride

HRID 911155Notes

Reaction equation

HRID 911155 reaction equation
[P:1]([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[N:23]=[C:22]([C:24]2[C:25]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]4[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[C:41]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)=[N:40][N:39]=4)=[CH:33][CH:32]=3)=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1)([O:8]C(C)(C)C)([O:3]C(C)(C)C)=[O:2].[ClH:54]>O1CCOCC1>[ClH:54].[ClH:54].[P:1]([OH:8])([OH:3])([O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]1[N:23]=[C:22]([C:24]2[C:25]([O:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38]4[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[C:41]([C:48]5[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=5)=[N:40][N:39]=4)=[CH:33][CH:32]=3)=[N:26][CH:27]=[CH:28][CH:29]=2)[CH:21]=[CH:20][N:19]=1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66731722Di-tert-butyl 3-(4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylamino)propyl phosphate

Product 1

HCID 667314933-(4-(2-(4-(4-Phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylamino)propyl dihydrogen phosphate dihydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of di-tert-butyl 3-(4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylamino)propyl phosphate (95 mg, 0.13 mmol) in 1,4-dioxane (3.7 ml, 0.04 M) under nitrogen was added 4M HCl in Dioxane (0.23 mL, 0.91 mmol). Reaction stirred at RT for 18 hrs. The mixture appeared heterogeneous, and the solids were filtered, washed with dioxane and ether, and dried under reduced pressure to afford 3-(4-(2-(4-(4-phenylphthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylamino)propyl dihydrogen phosphate dihydrochloride as a yellow solid. Mass of the title compound was obtained as the free base: MS m/z=622 [M+H]+. Calc'd for C32H30Cl2N7O5P: 621.6.

Workup

  1. customReaction
  2. filtrationthe solids were filtered
  3. washwashed with dioxane and ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-cd2238f6b71c4a2ca61d009511e81e6d
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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