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

HRID 593970Notes

Reaction equation

HRID 593970 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 C32H30C12N7O5P: 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-2957ee3350134e9d958be3753994a5aa
Source dataset
uspto-grants-2016_01
Patent number
US09242961B2

Reaction notes

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