Hydrochloric Acid → HCID 71572442, compound

HRID 712427Notes

Reaction equation

HRID 712427 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][CH:27]5[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH:26]5[CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(Cl)Cl.CO.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[CH2:29][CH2:28][CH:27]5[CH2:30][CH2:31][NH:32][CH:26]5[CH2:25]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6344DichloromethaneHCID 86729479HCID 86729479, compound

Product 1

HCID 71572442HCID 71572442, compoundYield 124.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 6-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy) propyl)octahydro-1H-pyrrolo[2,3-c]pyridine-1-carboxylate (1.16 g) in the mixture solvent of CH2Cl2 and MeOH was added a solution of HCl in EtOAc (30 mL). The reaction mixture was stirred at room temperature for 4 h, and filtered to give the title compound as a solid (1.20 g, 100%), HPLC: 99.69%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 486.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.45 (m, 2H), 1.78 (m, 3H), 1.80 (m, 2H), 2.10 (m, 1H), 2.42 (m, 5H), 2.82 (m, 3H), 4.03 (s, 3H), 4.10 (m, 2H), 6.76 (s, 1H), 7.16 (d, J=8.2 Hz, 1H), 7.24 (s, 1H), 7.28 (d, J=8.2 Hz, 1H), 7.41 (s, 1H), 8.54 (s, 1H) ppm.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-5190a1f8854b4725a4d4e7ca22734017
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…