Hydrochloric Acid → HCID 118524533, compound

HRID 1051903Notes

Reaction equation

HRID 1051903 reaction equation
[Br:1][C:2]1[C:25]([Br:26])=[CH:24][C:5]2[N:6]([CH2:22][CH3:23])[C:7]([N:9]3[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]3)=[N:8][C:4]=2[C:3]=1[C:27]#[N:28].[ClH:29].C(OCC)C>O1CCOCC1>[ClH:29].[Br:1][C:2]1[C:25]([Br:26])=[CH:24][C:5]2[N:6]([CH2:22][CH3:23])[C:7]([N:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:8][C:4]=2[C:3]=1[C:27]#[N:28]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 90240556HCID 90240556, compound

Product 1

HCID 118524533HCID 118524533, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-butyl 4-(5,6-dibromo-4-cyano-1-ethyl-1H-1,3-benzodiazol-2-yl)piperazine-1-carboxylate (Method 8A) (900 mg, 2.18 mmol) was dissolved in 1,4-dioxane (5.0 ml) and 4M HCl in dioxane (2.0 ml) was added. The mixture was stirred at room temperature until the reaction was complete (18 hrs) by LC/MS. Diethyl ether (10.0 ml) was added, product was filtered off, washed with diethyl ether and dried to afford 5,6-dibromo-1-ethyl-2-(piperazin-1-yl)-1H-1,3-benzodiazole-4-carbonitrile hydrochloride (820 mg, 1.8 mmol) 1H NMR (600 MHz, DMSO) δ 9.47 (s, 2H), 8.24 (s, 1H), 4.17 (q, J=7.2 Hz, 2H), 3.67-3.62 (m, 4H), 3.29 (s, 4H), 1.32 (t, J=7.2 Hz, 3H), m/z 413.9; rt 2.2.

Workup

  1. custom(18 hrs)
  2. filtrationproduct was filtered off
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-7681c0595b0d4081aaeefa07f186c5e4
Source dataset
uspto-grants-2016_07
Patent number
US09388192B2

Reaction notes

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