Hydrochloric Acid → HCID 71573030, compound

HRID 712521Notes

Reaction equation

HRID 712521 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1)#[CH:2].Cl>C(Cl)Cl.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([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[CH2:25][CH:26]5[CH:27]([CH2:29][NH:30][CH2:31]5)[CH2:28]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86729520HCID 86729520, compound

Product 1

HCID 71573030HCID 71573030, compoundYield 91.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(3-((4-((3-ethynylphenyl)amino)-7-methoxyquinazolin-6-yl)oxy) propyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.22 g) in DCM (30 mL) was added a solution of HCl in EtOAc at room temperature. The reaction mixture was stirred for 6 h at room temperature and filtered to give crude product. The crude product was recrystallized from a mixture of MeOH and EA to give the title compound as a white solid (0.91 g, 90.50%), HPLC: 94.65%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 444.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.84-1.89 (m, 4H), 2.38-2.44 (m, 6H), 2.69-2.76 (m, 4H), 3.95 (s, 3H), 4.03 (s, 1H), 4.14 (t, J=7.2 Hz, 2H), 7.13 (s, 1H), 7.25 (s, 1H), 7.43 (s, 1H), 7.55-7.60 (m, 1H), 7.90-7.93 (m, 1H), 8.68 (s, 1H) ppm.

Workup

  1. filtrationfiltered
  2. customto give crude product
  3. customThe crude product was recrystallized from a mixture of MeOH and EA

Sources & evidence

ORD record
ord-bc5b5f57a0d849b5b62860c57bf64439
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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