Hydrochloric Acid → HCID 122512303, compound

HRID 1479108Notes

Reaction equation

HRID 1479108 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[CH2:41][C:31]2=[C:32]3[N:37]([N:38]=[C:30]2[CH2:29]1)[CH:36]=[C:35]([Cl:39])[C:34]([CH3:40])=[N:33]3)=[O:27])C)(C)(C)C>C(Cl)Cl>[ClH:39].[Cl:39][C:35]1[C:34]([CH3:40])=[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])[CH2:41][C:31]3=2)[CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131736564HCID 131736564, compound

Product 1

HCID 122512303HCID 122512303, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4M solution of HCl in 1,4-dioxane (456 μL; 1.83 mmol; 10 eq.) was added to solution of {2-[2-(6-chloro-5-methyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-5-fluoro-phenoxy]-ethyl}-methyl-carbamic acid tert-butyl ester (92 mg; 0.18 mmol; 1 eq.) in DCM (2 mL) and the reaction mixture was stirred at room temperature for 30 minutes then concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (15 mg, 19%) as a yellow solid. 1H NMR (DMSO-d6) δ 9.55-9.45 (d, J=5.0 Hz, 1H), 9.01-8.78 (s, 2H), 7.43 (ddd, J=8.4, 6.7, 4.5 Hz, 1H), 7.19 (dd, J=11.1, 2.3 Hz, 1H), 6.95 (td, J=8.5, 2.3 Hz, 1H), 4.82 (d, J=5.8 Hz, 2H), 4.58 (d, J=12.5 Hz, 2H), 4.36 (t, J=4.5 Hz, 2H), 3.26 (t, J=5.2 Hz, 2H), 2.60 (s, 1.5H), 2.57-2.51 (m, 4.5H). HPLC (max plot) 99.2%, Rt 2.48 min. UPLC/MS: (MS+) 404.3 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customPurification by mass

Sources & evidence

ORD record
ord-6d14b9cadce545f1bf16df79e0dd9a14
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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