Hydrochloric Acid → HCID 71572439, compound

HRID 712457Notes

Reaction equation

HRID 712457 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[CH2:29][CH2:28][CH2:27][CH:26]5[CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][CH:25]45)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].Cl>C(Cl)Cl>[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[CH2:29][CH2:28][CH2:27][CH:26]5[CH2:30][NH:31][CH2:32][CH:25]45)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86729493HCID 86729493, compound

Product 1

HCID 71572439HCID 71572439, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 1-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydro-1H-pyrrolo[3,4-b]pyridine-6(2H)-carboxylate (0.60 g) in CH2Cl2 was added a solution of 3M HCl in EtOAC. Solid was precipitated out after 2 h reaction. The reaction mixture was filtered, and the residue was dried to give the title compound as a yellow solid (0.50 g, 80.00%), HPLC: 96.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 486.3 (M+1); 1H NMR (400 MHz, d6-DMSO) δ: 1.99 (m, 3H), 1.56 (m, 2H), 1.94-1.98 (m, 2H), 2.19 (d, J=4.8 Hz, 1H), 2.50-2.53 (m, 2H), 2.85-2.87 (m, 2H), 2.91-2.95 (m, 1H), 3.37 (s, 3H), 4.05-4.07 (m, 3H), 4.13-4.14 (m, 1H), 4.15-4.17 (m, 2H), 7.44 (s, 1H), 7.50 (t, J=4.4 Hz, 1H), 7.83-7.88 (m, 1H), 8.07-8.09 (m, 1H), 8.99-9.02 (m, 1H), 9.15 (s, 1H) ppm.

Workup

  1. customSolid was precipitated out after 2 h
  2. customreaction
  3. filtrationThe reaction mixture was filtered
  4. customthe residue was dried

Sources & evidence

ORD record
ord-f00cd59204a944659030dff3d6b4b91c
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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