Triethylamine → HCID 178504990, compound

HRID 1644607Notes

Reaction equation

HRID 1644607 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[C:8]([C:13]2[CH:14]=[C:15]([CH:17]=[C:18]([C:20]3[NH:28][C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:19]=2)[NH2:16])=[N:9][CH:10]=[CH:11][CH:12]=1.CCN(CC)CC.[NH4+].[Cl-]>C(Cl)Cl>[Cl:6][C:7]1[C:8]([C:13]2[CH:14]=[C:15]([NH:16][S:2]([CH3:1])(=[O:4])=[O:3])[CH:17]=[C:18]([C:20]3[NH:28][C:23]4=[N:24][CH:25]=[CH:26][CH:27]=[C:22]4[N:21]=3)[CH:19]=2)=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 178507329HCID 178507329, compound

Product 1

HCID 178504990HCID 178504990, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (10.0 μL, 0.12 mmol) was added to a solution of Example 183 (32.1 mg, 0.1 mmol) in CH2Cl2 (2 mL) followed by Et3N (20.0 μL, 0.15 mmol) at 0° C. The resulting mixture was stirred overnight and saturated NH4Cl solution (50 mL) was added and the mixture extracted with CH2Cl2 (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The resulting material was purified by LCMS (acetonitrile-water gradient) to give the title compound (15 mg, 38%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.99 (s, 3H) 7.33 (dd, J=7.21, 4.42, Hz, 1 H) 7.52 (dd, J=5.27, 3.48 Hz, 1 H) 7.83 (t, J=5.21 Hz, 1 H) 7.87 (d, J=5.11 Hz, 2 H) 8.03 (t, J=5.11 Hz, 1 H) 8.21 (t, J=5.11 Hz, 1 H) 8.34 (d, J=5.11 Hz, 2 H) 8.51 (d, J=5.42, Hz, 1 H) 8.56 (d, J=5.91 Hz, 1 H). MS (ES) [M+H] calculated for C18H15ClN5O2S, 400.06; found 400.02.

Workup

  1. extractionthe mixture extracted with CH2Cl2 (3×50 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by LCMS (acetonitrile-water gradient)

Sources & evidence

ORD record
ord-654c9c4e9c3e44438464a78582e1db86
Source dataset
uspto-grants-2012_02
Patent number
US08124617B2

Reaction notes

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