Triethylamine → HCID 57990011, compound

HRID 1962027Notes

Reaction equation

HRID 1962027 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)=[N:11][C:10]=2[C:20]2[C:21]([F:38])=[C:22]([NH:26][S:27]([C:30]3[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=3[F:37])(=[O:29])=[O:28])[CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.[CH:46]1([C:51](Cl)=[O:52])[CH2:50][CH2:49][CH2:48][CH2:47]1>ClCCl>[F:37][C:31]1[CH:32]=[CH:33][C:34]([F:36])=[CH:35][C:30]=1[S:27]([NH:26][C:22]1[C:21]([F:38])=[C:20]([C:10]2[N:11]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[S:13][C:9]=2[C:7]2[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][NH:1][C:51]([CH:46]3[CH2:50][CH2:49][CH2:48][CH2:47]3)=[O:52])[N:8]=2)[CH:25]=[CH:24][CH:23]=1)(=[O:28])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 57989626HCID 57989626, compound

Product 1

HCID 57990011HCID 57990011, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N-{3-[5-[2-(aminomethyl)-4-pyrimidinyl]-2-(4-morpholinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide (0.1 g, 0.178 mmol) in dichloromethane (1.270 ml) was added triethylamine (0.062 ml, 0.444 mmol). A solution of cyclopentanecarbonyl chloride (0.024 g, 0.178 mmol) in dichloromethane (0.508 ml) was added dropwise and stirred. The reaction was quenched with water, extracted 2× with DCM, the organic extracts dried over MgSO4, filtered, and concentrated. The crude product was added to a silica gel column and eluted with DCM with MeOH (0% to 10%) and collected fractions to obtain the title compound as a solid (30 mg, 25% yield). MS (ESI): 659 [M+H]+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted 2× with DCM
  3. dry with materialthe organic extracts dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additionThe crude product was added to a silica gel column
  7. washeluted with DCM with MeOH (0% to 10%)
  8. customcollected fractions

Sources & evidence

ORD record
ord-a0174e8abb8f4bf2bc03943c020dba2b
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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