Hydrochloric Acid → HCID 71573261, compound

HRID 712421Notes

Reaction equation

HRID 712421 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:39][CH3:40])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH:26]5[CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31][CH:25]45)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].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:39][CH3:40])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH2:27][CH:26]5[CH2:29][NH:30][CH2:31][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 86729476HCID 86729476, compound

Product 1

HCID 71573261HCID 71573261, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 1-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate (0.50 g) was added a solution of HCl in EtOAc (10 mL). The reaction mixture was continued to stir at room temperature for 2 h and filtered to afford the title compound as a solid (0.28 g, 64.00%), HPLC: 98.79%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 472.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.55-1.58 (m, 2H), 1.83-1.88 (m, 3H), 2.25 (t, J=5.7 Hz, 2H), 2.40-2.45 (m, 3H), 2.70-2.73 (m, 4H), 3.93 (s, 3H), 4.08 (t, J=5.4 Hz, 2H), 7.16 (s, 1H), 7.26 (s, 1H), 7.45 (s, 1H), 7.57-7.60 (m, 1H), 7.91-7.95 (m, 1H), 8.64 (s, 1H) ppm.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-4cd23a70ecfc4c7f8503e56224b21c38
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…