Hydrochloric Acid → HCID 86729518, compound

HRID 712519Notes

Reaction equation

HRID 712519 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:40][CH3:41])=[C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:29][CH:28]5[CH2:30][N:31](C(OC(C)(C)C)=O)[CH2:32][CH:27]5[CH2:26]4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[CH:2].Cl>C(Cl)Cl.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:40][CH3:41])=[C:18]([O:21][CH2:22][CH2:23][CH2:24][N:25]4[CH2:26][CH:27]5[CH:28]([CH2:30][NH:31][CH2:32]5)[CH2:29]4)[CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[F:9])#[CH:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86729519HCID 86729519, compound

Product 1

HCID 86729518HCID 86729518, compoundYield 92.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(3-((4-((3-ethynyl-4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy)propyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.03 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 (0.78 g, 92.60%), HPLC: 95.04%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 462.2 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.83-1.88 (m, 4H), 2.32-2.45 (m, 6H), 2.66-2.76 (m, 4H), 4.03 (s, 3H), 4.06 (s, 1H), 4.15 (t, J=7.2 Hz, 2H), 7.15 (s, 1H), 7.23 (s, 1H), 7.40 (s, 1H), 7.53-7.60 (m, 1H), 7.90-7.93 (m, 1H), 8.66 (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-b0900313e3ee4c3885304971106f6977
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

Loading…