Hydrochloric Acid → HCID 86729475, compound

HRID 712419Notes

Reaction equation

HRID 712419 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][CH:27]5[CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31][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].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:39][CH3:40])=[C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]4[CH2:28][CH:27]5[CH:26]([CH2:31][NH:30][CH2:29]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 78135273HCID 78135273, compound

Product 1

HCID 86729475HCID 86729475, compoundYield 92.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(3-((4-((3-chloro-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.70 g) in DCM (30 mL) was added a solution of HCl in EtOAc. The reaction mixture was stirred at room temperature for 6 h and filtered to obtain the crude product. The crude product was recrystallized from MeOH/EA to give the title compound as a white solid (1.30 g, 80.00%), HPLC: 85.68%. 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: 1.81-1.88 (m, 4H), 2.35-2.43 (m, 6H), 2.68-2.74 (m, 4H), 3.99 (s, 3H), 4.13 (t, J=7.2 Hz, 2H), 7.16 (s, 1H), 7.26 (s, 1H), 7.45 (s, 1H), 7.57-7.62 (m, 1H), 7.91-7.93 (m, 1H), 8.64 (s, 1H) ppm.

Workup

  1. filtrationfiltered
  2. customto obtain the crude product
  3. customThe crude product was recrystallized from MeOH/EA

Sources & evidence

ORD record
ord-65ef2b1d252e4d37a5692e8cc9f531b1
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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