Water → 2-(1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)1H-pyrazol-4-yl)ethyl methanesulfonate

HRID 1162786

Reaction equation

HRID 1162786 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:5]([C:25]([F:28])([F:27])[F:26])=[N:6][N:7]([CH2:9][C:10]([NH:12][C:13]2[S:17][C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[C:14]=2[C:22]([NH2:24])=[O:23])=[O:11])[CH:8]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38].O>C(Cl)Cl>[CH3:36][S:37]([O:1][CH2:2][CH2:3][C:4]1[C:5]([C:25]([F:26])([F:28])[F:27])=[N:6][N:7]([CH2:9][C:10]([NH:12][C:13]2[S:17][C:16]3[CH2:18][CH2:19][CH2:20][CH2:21][C:15]=3[C:14]=2[C:22](=[O:23])[NH2:24])=[O:11])[CH:8]=1)(=[O:39])=[O:38]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 595204772-(2-(4-(2-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

Product 1

HCID 595204612-(1-(2-(3-carbamoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-ylamino)-2-oxoethyl)-3-(trifluoromethyl)1H-pyrazol-4-yl)ethyl methanesulfonateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-(4-(2-Hydroxyethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (Example 64, 480 mg, 1.153 mmol) was dissolved in DCM (10 mL). Triethylamine (117 mg, 1.153 mmol) was added, followed by methanesulfonyl chloride (132 mg, 1.153 mmol). The reaction mixture was stirred at RT for 3 h. Water was added and the reaction mixture extracted with DCM (×3). The combined DCM layers were then washed with brine, dried over MgSO4, filtered and the solvent removed in vacuo to yield the desired product (450 mg, 0.91 mmol, 79%).

Workup

  1. extractionthe reaction mixture extracted with DCM (×3)
  2. washThe combined DCM layers were then washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-e4f6d115e4d646668db695925a99d421
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Linked notes

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