Hydrochloric Acid → HCID 71572914, compound

HRID 712516Notes

Reaction equation

HRID 712516 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:38][CH3:39])=[C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:27][CH:26]5[CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH:25]5[CH2:24]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.Cl>C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:38][CH3:39])=[C:16]([O:19][CH2:20][CH2:21][CH2:22][N:23]4[CH2:24][CH:25]5[CH:26]([CH2:28][NH:29][CH2:30]5)[CH2:27]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86729517HCID 86729517, compound

Product 1

HCID 71572914HCID 71572914, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl 5-(3-((4-((4-fluorophenyl)amino)-7-methoxyquinazolin-6-yl)oxy) propyl)hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (1.14 g) in DCM (30 mL) was added a solution of HCl in EtOAc. 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 (0.83 g, 89.50%), HPLC: 95.23%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 438.2 (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), 4.15 (t, J=7.2 Hz, 2H), 7.15 (s, 1H), 7.23 (s, 1H), 7.40 (s, 1H), 7.53-7.60 (m, 2H), 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-878e4c07b82f4b728e9b6392921ad1ca
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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