Hydrochloric Acid → HCID 131736567, compound

HRID 1479110Notes

Reaction equation

HRID 1479110 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:22]([N:24]2[CH2:38][C:27]3=[C:28]4[N:33]([N:34]=[C:26]3[CH2:25]2)[C:32]([CH3:35])=[C:31]([Cl:36])[C:30]([CH3:37])=[N:29]4)=[O:23])[CH:11]([C:39]([F:42])([F:41])[F:40])[CH2:10]1)=O)(C)(C)C>O1CCOCC1>[ClH:36].[Cl:36][C:31]1[C:30]([CH3:37])=[N:29][C:28]2[N:33]([N:34]=[C:26]3[CH2:25][N:24]([C:22]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[O:15][CH:12]4[CH2:13][CH2:14][NH:9][CH2:10][CH:11]4[C:39]([F:41])([F:40])[F:42])=[O:23])[CH2:38][C:27]3=2)[C:32]=1[CH3:35]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131736568HCID 131736568, compound

Product 1

HCID 131736567HCID 131736567, compoundYield 122.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4M solution of HCl in 1,4-dioxane (4 mL; 16 mmol; 82 eq.) was added to a solution of 4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxy]-3-trifluoromethyl-piperidine-1-carboxylic acid tert-butyl ester (116 mg; 0.20 mmol; 1 eq.) in 1,4-dioxane (2 mL) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. Crystallization from cold iPrOH afforded the title compound (65 mg, 62%) as a white solid. 1H NMR (DMSO-d6) δ 9.14 (s, 2H), 7.48 (d, J=7.6 Hz, 1H), 7.44-7.34 (m, 1H), 7.30 (d, J=8.5 Hz, 1H), 7.15 (t, J=7.4 Hz, 1H), 5.23 (br s, 1H), 4.87 (d, J=6.3 Hz, 2H), 4.63-4.34 (m, 2H), 3.52-3.38 (m, 1H), 3.31-3.23 (m, 1H), 3.20-2.88 (m, 3H), 2.85 (s, 1.5H), 2.81 (s, 1.5H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.16-2.03 (m, 1H), 2.00-1.86 (m, 1H). HPLC (max plot) 96.5%, Rt 3.12 min. UPLC/MS: (MS+) 494.3 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customCrystallization from cold iPrOH

Sources & evidence

ORD record
ord-64c1d00777e4475cb8509dc2ec35795a
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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