Hydrochloric Acid → HCID 86729490, compound

HRID 712454Notes

Reaction equation

HRID 712454 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]([N:27](C(OC(C)(C)C)=O)[CH2:28][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].Cl>C(Cl)Cl.CO>[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]([NH:27][CH2:28][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 86729491HCID 86729491, compound

Product 1

HCID 86729490HCID 86729490, compoundYield 140.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 6-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)octahydro-1H-pyrrolo[3,4-b]pyridine-1-carboxylate (0.60 g) in CH2Cl2 was added a saturated solution of HCl in MeOH. 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 pale yellow solid (0.70 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, CDCl3) δ: 1.13-1.96 (m, 6H), 2.09-2.43 (m, 2H), 3.29 (m, 2H), 3.68-3.70 (m, 6H), 3.83 (s, 3H), 4.06 (m, 2H), 6.93 (t, J=8.2 Hz, 1H), 7.06 (s, 1H), 7.27 (m, 1H), 7.44 (d, J=8.0 Hz, 1H), 7.87 (d, J=4.2 Hz, 1H), 8.45 (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-2ceae850e2dc4c50a1bcb0c0edbc9d84
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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