Hydrochloric Acid → HCID 11238039, compound

HRID 857954Notes

Reaction equation

HRID 857954 reaction equation
Cl.[P:2]([O:14][CH2:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][C:34]=2[O:35][CH3:36])[N:31]=[CH:30][N:29]=[C:28]3[NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[C:39]=2[F:45])[CH2:20][CH2:19]1)=[O:17])([O:9]C(C)(C)C)([O:4]C(C)(C)C)=[O:3].C(OCC)C>O1CCOCC1>[P:2]([OH:4])([OH:9])([O:14][CH2:15][C:16]([N:18]1[CH2:19][CH2:20][CH:21]([O:24][C:25]2[CH:26]=[C:27]3[C:32](=[CH:33][C:34]=2[O:35][CH3:36])[N:31]=[CH:30][N:29]=[C:28]3[NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[C:39]=2[F:45])[CH2:22][CH2:23]1)=[O:17])=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 69433554HCID 69433554, compound

Product 1

HCID 11238039HCID 11238039, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4M Hydrogen chloride in 1,4 dioxane (1.95 ml) was added to a stirred solution of di-tert-butyl 2-[4-(4-[3-chloro-2-fluoroanilino]-7-methoxyquinazolin-6-yloxy)piperidin-1-yl]-2-oxoethyl phosphate (0.951 g) in 1,4-dioxane (16 ml). The mixture was stirred overnight and diethyl ether (50 ml) was then added. The resulting precipitate was collected by filtration and dried to give the title product as a white solid (0.77 g); NMR Spectrum: (DMSO d6) 1.60–1.76 (m, 2H), 2.11 (m, 2H), 3.38 (m, 2H), 3.69 (m, 1H), 3.91 (m, 1H), 4.02 (s, 3H), 4.53 (m, 2H), 5.02 (m, 1H), 7.37 (m, 2H), 7.55 (m, 1H), 7.65 (m, 1H), 8.53 (s, 1H), 8.81 (s, 1H), 11.86 (br s, 1H); Mass Spectrum: (M+H)+ 541.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-ff6821e7d2e14388b41a6a8bc6d94319
Source dataset
uspto-grants-2006_12
Patent number
US07148230B2

Reaction notes

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