Hydrochloric Acid → HCID 89662805, compound

HRID 1479090Notes

Reaction equation

HRID 1479090 reaction equation
C(OC([N:8]1[CH:14]([C:15]([F:18])([F:17])[F:16])[CH2:13][CH2:12][N:11]([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])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.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[N:11]4[CH2:12][CH2:13][CH:14]([C:15]([F:17])([F:18])[F:16])[NH:8][CH2:9][CH2:10]4)=[O:26])[CH2:41][C:30]3=2)[C:35]=1[CH3:38]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-Dioxane2×HCID 122512309HCID 122512309, compound

Product 1

HCID 89662805HCID 89662805, compoundYield 18.9%

Procedure

A suspension of 4-[2-(6-chloro-5,7-dimethyl-1H,3H-2,4,7a,8-tetraaza-cyclopenta[a]indene-2-carbonyl)-phenyl]-7-trifluoromethyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester (90 mg; 0.15 mmol; 1 eq.) in a 4M solution of HCl in 1,4-dioxane (0.38 mL; 1.52 mmol; 10 eq.) was stirred at room temperature for 3 hours. A 4M solution of HCl in 1,4-dioxane (0.38 mL; 1.52 mmol; 10 eq.) was added and the reaction mixture was stirred at room temperature for a 45 minutes. After concentration in vacuo, purification by mass directed preparative HPLC afforded the title compound (14 mg, 17%) as a white solid. 1H NMR (DMSO-d6) 10.12 (br s, 2H), 7.46-7.35 (m, 1H), 7.35-7.26 (m, 1H), 7.18-7.10 (m, 1H), 7.04 (t, J=7.4 Hz, 1H), 4.85 (d, J=8.3 Hz, 2H), 4.67-4.28 (m, 3H), 4.22-3.74 (m, 4H), 3.62-3.45 (m, 2H), 2.85 (s, 1.5H), 2.81 (s, 1.5H), 2.62 (s, 1.5H), 2.56 (s, 1.5H), 2.34-2.19 (m, 1H), 2.17-1.98 (m, 1H). HPLC (max plot) 94.6%, Rt 2.94 min. UPLC/MS: (MS+) 493.2 ([M+H]+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a 45 minutes
  2. concentrationAfter concentration
  3. customin vacuo, purification by mass

Sources & evidence

ORD record
ord-d4da6da1c25944f48883420ddf6f5bb0
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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