Hydrochloric Acid → HCID 122436167, compound

HRID 1479113Notes

Reaction equation

HRID 1479113 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][C:11]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]([N:27]2[CH2:41][C:30]3=[C:31]4[N:36]([N:37]=[C:29]3[CH2:28]2)[C:35]([CH3:38])=[C:34]([Cl:39])[C:33]([CH3:40])=[N:32]4)=[O:26])([C:14]([F:17])([F:16])[F:15])[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[Cl:39][C:34]1[C:33]([CH3:40])=[N:32][C:31]2[N:36]([N:37]=[C:29]3[CH2:28][N:27]([C:25]([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[O:18][C:11]4([C:14]([F:16])([F:15])[F:17])[CH2:12][CH2:13][NH:9][CH2:10]4)=[O:26])[CH2:41][C:30]3=2)[C:35]=1[CH3:38]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131736569HCID 131736569, compound

Product 1

HCID 122436167HCID 122436167, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of HCl in 1,4-dioxane (1.06 mL; 4.22 mmol; 25 eq.) was added to a solution of 3-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-3-trifluoromethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (98 mg; 0.17 mmol; 1 eq.) in 1,4-dioxane (10 mL) and the resulting mixture was stirred at room temperature for 20 hours then concentrated in vacuo. The residue was partitioned between DCM and sat. aq. NaHCO3 and the aqueous layer was extracted with DCM. The combined organic phase was washed with brine, dried over magnesium sulfate and concentrated in vacuo. Purification by mass directed preparative HPLC afforded the title compound (15 mg, 25%) as a white solid. HPLC (max plot) 95.9%, Rt 3.23 min. UPLC/MS: (MS+) 480.3 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between DCM and sat. aq. NaHCO3
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by mass

Sources & evidence

ORD record
ord-bd533f44ff2c4a328f8f3eed33a01a7e
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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