Triethylamine → HCID 24887022, compound

HRID 722261Notes

Reaction equation

HRID 722261 reaction equation
FC(F)(F)C(O)=O.[NH2:8][C@@H:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[NH:18][C:19]([C:21]1[NH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][C:26]([Cl:30])=[CH:25][CH:24]=2)=[O:20].CCN(CC)CC.[Cl:38][CH2:39][S:40](Cl)(=[O:42])=[O:41]>C1COCC1>[Cl:30][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:19]([NH:18][C@@H:10]1[CH2:11][C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C@H:9]1[NH:8][S:40]([CH2:39][Cl:38])(=[O:42])=[O:41])=[O:20])=[CH:29]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77054(Chloromethyl)sulfonyl chlorideHCID 69585785HCID 69585785, compound

Product 1

HCID 24887022HCID 24887022, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[(1R,2R)-1-Amino-2,3-dihydro-1H-inden-2-yl]-5-chloro-1H-indole-2-carboxamide trifluoroacetic acid salt (Method 5, 2.2 g, 5.0 mmol) and Et3N (2.1 mL, 15.0 mmol) dissolved in dry THF (30 mL) at 5° C., chloromethyl sulphonyl chloride (820 mg, 5.5 mmol) in dry THF (5 mL) was added and the reaction allowed to warm to ambient temperature for 2 hours. The volatiles were removed by evaporation under reduced pressure and the residue dissolved in EtOAc (75 mL), washed with water (2×25 mL), brine (25 mL) and dried (MgSO4). Removal of the volatiles under reduced pressure gave the title compound (2.16 g, 98%) as a buff powder.

Workup

  1. customThe volatiles were removed by evaporation under reduced pressure
  2. dissolutionthe residue dissolved in EtOAc (75 mL)
  3. washwashed with water (2×25 mL), brine (25 mL)
  4. dry with materialdried (MgSO4)
  5. customRemoval of the volatiles under reduced pressure

Sources & evidence

ORD record
ord-9b98d7f0f1c940cebd3ccfb35188d690
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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