Hydrochloric Acid → N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydro-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)propoxy)-7-methoxyquinazolin-4-amine

HRID 712471Notes

Reaction equation

HRID 712471 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:40][CH3:41])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:32][CH:31]5[CH:26]([CH2:27][N:28](C(OC(C)(C)C)=O)[CH2:29][CH2:30]5)[CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl>C(Cl)Cl.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:40][CH3:41])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:32][CH:31]5[CH:26]([CH2:27][NH:28][CH2:29][CH2:30]5)[CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86729495tert-butyl 2-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy) propyl)hexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate

Product 1

HCID 71571778N-(3-chloro-4-fluorophenyl)-6-(3-(hexahydro-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)propoxy)-7-methoxyquinazolin-4-amineYield 90.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 2-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy) propyl)hexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate (0.40 g) in CH2Cl2 was added a solution of HCl in EtOAc (3 M, 10 mL). White solid was precipitated out after 2 h reaction. The resulted mixture was filtered and the residue was dried to give the title compound as a pale yellow solid (0.30 g, 80.00%), HPLC: 99.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 486.2 (M+1); 1H NMR (400 MHz, D2O) δ: 1.97-2.03 (m, 4H), 2.68-2.71 (m, 2H), 2.80-2.86 (m, 4H), 2.87-2.91 (m, 2H), 3.40-3.45 (m, 2H), 4.07-4.11 (m, 2H), 4.19 (s, 3H), 4.39-4.43 (m, 2H), 7.441 (s, 1H), 7.50 (t, J=8.6 Hz, 1H), 7.84 (s, 2H), 8.68 (t, J=4.6 Hz, 1H), 8.89 (s, 1H) ppm.

Workup

  1. customWhite solid was precipitated out after 2 h
  2. customreaction
  3. filtrationThe resulted mixture was filtered
  4. customthe residue was dried

Sources & evidence

ORD record
ord-fc8d8f4d88d74d53b23d6e5693be6eab
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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