Hydrochloric Acid → HCID 131736560, compound

HRID 1479101Notes

Reaction equation

HRID 1479101 reaction equation
Cl.O1CCOCC1.C(O[C:13](=O)[N:14]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]([N:28]1[CH2:42][C:31]2=[C:32]3[N:37]([N:38]=[C:30]2[CH2:29]1)[C:36]([CH3:39])=[C:35]([Cl:40])[C:34]([CH3:41])=[N:33]3)=[O:27])C)(C)(C)C>C(Cl)Cl.CC(OC)(C)C>[ClH:40].[Cl:40][C:35]1[C:34]([CH3:41])=[N:33][C:32]2[N:37]([N:38]=[C:30]3[CH2:29][N:28]([C:26]([C:20]4[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=4[O:18][CH2:17][CH2:16][NH:14][CH3:13])=[O:27])[CH2:42][C:31]3=2)[C:36]=1[CH3:39]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89649699HCID 89649699, compound

Product 1

HCID 131736560HCID 131736560, compoundYield 139%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

A 4M solution of HCl in 1,4-dioxane (0.72 mL; 2.9 mmol; 15 eq.) was added to a solution of {2-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-phenoxy]-ethyl}-methyl-carbamic acid tert-butyl ester (100 mg; 0.19 mmol; 1 eq.) in DCM (5 mL) and the reaction mixture was stirred at room temperature for 2 hours. The residue was suspended in hot MTBE, filtered and dried to afford the title compound (60 mg, 68%) as a pale yellow solid. 1H NMR (DMSO-d6) δ 8.92-8.69 (m, 2H), 7.50-7.38 (m, 1H), 7.24-7.13 (m, 1H), 7.00-6.90 (td, J=8.5, 8.0, 2.2 Hz, 1H), 4.89-4.77 (d, J=8.6 Hz, 2H), 4.65-4.51 (m, 2H), 4.41-4.32 (m, 2H), 3.27 (br s, 2H), 2.85 (s, 1.7H), 2.81 (s, 1.3H), 2.62 (s, 1.3H), 2.57 (s, 1.7H), 2.53 (s, 3H). HPLC (max plot) 97.0%, Rt 2.73 min. UPLC/MS: (MS+) 418.3 ([M+H]+).

Workup

  1. filtrationfiltered
  2. customdried

Sources & evidence

ORD record
ord-d6c2bb6d765a4cbfa9b8bf89dfd90b08
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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