Hydrochloric Acid → HCID 122429366, compound

HRID 1479104Notes

Reaction equation

HRID 1479104 reaction equation
[ClH:1].C(OC(=O)[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][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])[CH2:11][CH2:10]1)(C)(C)C>O1CCOCC1>[ClH:36].[ClH:1].[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([CH2:15][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])[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 89649695HCID 89649695, compound

Product 1

HCID 122429366HCID 122429366, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A 4N solution of HCl in dioxane (1.0 mL, 4 mmol) was added to a solution of {1-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-benzyl]-piperidin-4-yl}-carbamic acid tert-butyl ester (136 mg, 0.24 mmol) in dioxane (1.0 mL). After 3 hours of stirring at RT, the precipitate was filtered off and washed with dioxane (2×). The solid was dissolved in water (2 ml) and lyophilized to give the title compound as an off-white powder (82 mg, 64%). 1H NMR (300 MHz, DMSO-d6) δ 10.97-10.60 (m, 1H), 8.63-8.24 (m, 3H), 8.15-7.98 (m, 1H), 7.76-7.41 (m, 3H), 5.08-4.86 (m, 2H), 4.73-4.48 (m, 2H), 4.44-4.17 (m, 2H), 3.60-2.96 (m, 5H), 2.85 (s, 1.5H), 2.81 (s, 1.5H), 2.63 (s, 1.5H), 2.56 (s, 1.5H), 2.23-1.78 (m, 4H). HPLC (max plot) 96.1%, Rt 2.23 min. UPLC/MS: (MS+) 439.4 ([M+H]+).

Workup

  1. filtrationthe precipitate was filtered off
  2. washwashed with dioxane (2×)
  3. dissolutionThe solid was dissolved in water (2 ml)

Sources & evidence

ORD record
ord-1d0f3d039910452e89ca68356c550452
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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