Hydrochloric Acid → HCID 71610249, compound

HRID 1479076Notes

Reaction equation

HRID 1479076 reaction equation
Cl.C(OC([N:9]1[CH2:14][CH2:13][O:12][CH:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:23]([N:25]2[CH2:39][C:28]3=[C:29]4[N:34]([N:35]=[C:27]3[CH2:26]2)[C:33]([CH3:36])=[C:32]([Cl:37])[C:31]([CH3:38])=[N:30]4)=[O:24])[CH2:10]1)=O)(C)(C)C.O>O1CCOCC1>[Cl:37][C:32]1[C:31]([CH3:38])=[N:30][C:29]2[N:34]([N:35]=[C:27]3[CH2:26][N:25]([C:23]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[O:16][CH2:15][CH:11]4[O:12][CH2:13][CH2:14][NH:9][CH2:10]4)=[O:24])[CH2:39][C:28]3=2)[C:33]=1[CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 131736550HCID 131736550, compound

Product 1

HCID 71610249HCID 71610249, compoundYield 112.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A 4M solution of HCl in 1,4-dioxane (0.6 mL; 2.39 mmol; 4 eq.) was added to a suspension of 2-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenoxymethyl]-morpholine-4-carboxylic acid tert-butyl ester (366 mg; 0.6 mmol; 1 eq.) in 1,4-dioxane (3 mL) followed by water (304) and the resulting mixture was stirred at room temperature for 16 hours. A 4M solution of HCl in 1,4-dioxane (0.3 mL; 1.2 mmol; 2 eq.) was added and the resulting mixture was stirred at room temperature for 3 hours. Concentration in vacuo afforded the title compound (298 mg, quantitative) as an orange solid. 1H NMR (DMSO-d6) δ 7.46 (t, J=7.9 Hz, 1H), 7.38-7.28 (m, 1H), 7.15 (d, J=8.5 Hz, 1H), 7.08 (t, J=7.4 Hz, 1H), 4.95-4.77 (m, 2H), 4.69-4.39 (m, 2H), 4.27-4.06 (m, 2H), 4.06-3.87 (m, 1H), 3.77-3.53 (m, 2H), 3.30-3.17 (m, 1H), 3.12-2.94 (m, 1H), 2.92-2.74 (m, 4H), 2.72-2.53 (m, 4H). HPLC (max plot) 99.5%, Rt 2.70 min. UPLC/MS: (MS+) 442.4 ([M+H]+).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 3 hours
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-f47ec14c7513419a880a78900efc74fb
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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