Potassium Carbonate → HCID 178504222, compound

HRID 45009Notes

Reaction equation

HRID 45009 reaction equation
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH:17]=[C:16]([C:18]3[C:19]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=4[N:21]=[CH:22][N:23]=3)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)(=O)=O.[NH2:35][C:36]1[NH:37][C:38]([SH:41])=[N:39][N:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:32][Si:31]([CH3:34])([CH3:33])[CH2:30][CH2:29][O:28][CH2:27][N:24]1[C:20]2[N:21]=[CH:22][N:23]=[C:18]([C:16]3[CH:15]=[N:14][N:13]([C@@H:10]4[CH2:11][CH2:12][C@H:7]([CH2:6][S:41][C:38]5[NH:37][C:36]([NH2:35])=[N:40][N:39]=5)[CH2:8][CH2:9]4)[CH:17]=3)[C:19]=2[CH:26]=[CH:25]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 178504221HCID 178504221, compoundHCID 178509207HCID 178509207, compound

Product 1

HCID 178504222HCID 178504222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

cis-4-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclohexylmethyl methanesulfonate (124.56 mg, 0.00024 mol), and 5-amino-4H-1,2,4-triazole-3-thiol (43.00 mg, 0.0003702 mol) were dissolved in DMF (1.20 mL) and potassium carbonate (0.122 g, 0.000887 mol) was added. The reaction was stirred at 50° C. for 18 h, at which time LCMS showed nearly complete reaction, and product present. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel using EtOAc as eluent to give the product. LC/MS (M+H)+: 526, 1H NMR(CDCl3): δ 8.90 (s, 1H), 8.40 (s, 1H), 8.30 (s, 1H), 7.45 (d, 1H), 6.87 (d, 1H), 5.73 (S, 2H), 4.45 (brs, 2H), 4.41 (m, 1H), 3.60 (m, 2H), 3.22 (d, 2H, J=7.2 Hz), 2.29 (m, 2H), 1.70-2.10 (m, 7H), 0.98 (m, 2H), 0.00 (s, 9H).

Workup

  1. customreaction, and product present
  2. extractionThe reaction was extracted with ethyl acetate
  3. washthe organic extracts were washed with water, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe concentrate was chromatographed on silica gel
  7. customto give the product

Sources & evidence

ORD record
ord-e945cc0fc3d74a74b804c761622c7ba9
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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