Hydrochloric Acid → HCID 131736552, compound

HRID 1479082Notes

Reaction equation

HRID 1479082 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([N:30]2[CH2:44][C:33]3=[C:34]4[N:39]([N:40]=[C:32]3[CH2:31]2)[C:38]([CH3:41])=[C:37]([Cl:42])[C:36]([CH3:43])=[N:35]4)=[O:29])[CH:17]([F:45])[CH2:16]1)=O)(C)(C)C>>[ClH:42].[Cl:42][C:37]1[C:36]([CH3:43])=[N:35][C:34]2[N:39]([N:40]=[C:32]3[CH2:31][N:30]([C:28]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[O:21][CH:18]4[CH2:19][CH2:20][NH:15][CH2:16][CH:17]4[F:45])=[O:29])[CH2:44][C:33]3=2)[C:38]=1[CH3:41]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89650157HCID 89650157, compound

Product 1

HCID 131736552HCID 131736552, compoundYield 201%

Procedure

A 4M solution of HCl in 1,4-dioxane (10 mL; 400 mmol; 136 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-fluoro-piperidine-1-carboxylic acid tert-butyl ester (160 mg; 0.29 mmol; 1 eq.) and the reaction mixture was stirred at room temperature for 16 hours then concentrated in vacuo. The residue was triturated in Et2O and concentrated to dryness to afford the title compound (140 mg, 99%) as a pale yellow solid. UPLC/MS: (MS+) 444.4 ([M+H]+).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was triturated in Et2O
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-44c912c5c3af4bba9784f7b4bde90899
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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