Hydrochloric Acid → HCID 86732047, compound

HRID 1498787Notes

Reaction equation

HRID 1498787 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]3[N:21]([CH3:22])[C:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=4[N:18]=3)[N:11]=[C:10]([C:27]#[N:28])[N:9]=2)[N:3]=1.Cl.C([O-])(O)=[O:31].[Na+]>O1CCOCC1>[CH3:1][C:2]1[N:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[C:12]([C@@H:14]3[CH2:16][C@H:15]3[C:17]3[N:21]([CH3:22])[C:20]4[CH:23]=[CH:24][CH:25]=[CH:26][C:19]=4[N:18]=3)[N:11]=[C:10]([C:27]([NH2:28])=[O:31])[N:9]=2)[N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 71547617HCID 71547617, compound

Product 1

HCID 86732047HCID 86732047, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl)pyrimidine-2-carbonitrile (21) (50.0 mg, 0.135 mmol, 1.0 eq.) in 1,4-dioxane (0.30 mL) was added concentrated HCl (0.30 mL, 3.6 mmol, 27 eq) at room temperature. The resulting mixture was stirred at room temperature for 12 hours. After completion of the reaction, the mixture was neutralized with saturated aqueous NaHCO3 and extracted with DCM (2×30 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulphate, and concentrated under reduced pressure. The resulting residue was purified by silica gel preparative TLC (5% methanol in dichloromethane) to afford trans-4-(3,5-dimethyl-1H-1,2,4-triazol-1-yl)-6-(2-(1-methyl-1H-benzo[d]imidazol-2-yl)cyclopropyl) pyrimidine-2-carboxamide (22) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.02 (s, 1H), 7.69 (m, 1H), 7.59 (br d, 1H, J=3.2 Hz), 7.33-7.21 (m, 3H), 6.44 (br d, 1H, J=3.2 Hz), 3.82 (s, 3H), 3.01 (m, 1H), 3.00 (s, 3H), 2.90 (m, 1H), 2.42 (s, 3H), 2.16-2.07 (m, 2H). LRMS m/z (M+H) 389 found, 389 required. m.p. 119-121° C.

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with DCM (2×30 mL)
  3. washThe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel preparative TLC (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-ae69adb492f742a091b8ba1819ee8bda
Source dataset
uspto-grants-2015_12
Patent number
US09200001B2

Reaction notes

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