Triethylamine → HCID 131730181, compound

HRID 1809528Notes

Reaction equation

HRID 1809528 reaction equation
[C:1]([O:4][CH2:5][CH2:6][NH:7][C@H:8]1[C:16]2[C:11](=[C:12]([C:17]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[C:24]([C:32]#[N:33])[CH:23]=4)[O:19][N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)(=[O:3])[CH3:2].[CH3:34][S:35](Cl)(=[O:37])=[O:36].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][CH2:5][CH2:6][N:7]([C@H:8]1[C:16]2[C:11](=[C:12]([C:17]3[N:21]=[C:20]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH:29]([CH3:31])[CH3:30])=[C:24]([C:32]#[N:33])[CH:23]=4)[O:19][N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)[S:35]([CH3:34])(=[O:37])=[O:36])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58344747HCID 58344747, compound

Product 1

HCID 131730181HCID 131730181, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared using General Procedure 12. To a stirred solution of (R)-2-((4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)amino)ethyl acetate (20 mg, 0.04 mmol) in DCM (1 mL) was added methanesulfonyl chloride (10.2 mg, 0.08 mmol) followed by triethylamine (9.08 mg, 0.08 mmol)) at 0° C. The reaction mixture was stirred at room temperature for 16 h. The reaction was quenched with water (1 mL), extracted with DCM (2×1 mL), and the combined extracts were dried over MgSO4. The organic layers were concentrated to give 23 mg (50%) of (R)-2-(N-(4-(5-(3-cyano-4-isopropoxyphenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-yl)methylsulfonamido)ethyl acetate which was used in the next step without purification. LCMS-ESI (m/z) calculated for C26H28N4O6S: 524.2; found 547.1 [M+Na]+, tR=3.82 min.

Workup

  1. customPrepared
  2. customat 0° C
  3. customThe reaction was quenched with water (1 mL)
  4. extractionextracted with DCM (2×1 mL)
  5. dry with materialthe combined extracts were dried over MgSO4
  6. concentrationThe organic layers were concentrated

Sources & evidence

ORD record
ord-4bcb153a327d4e54a30d38047243cf8f
Source dataset
uspto-grants-2013_01
Patent number
US08362048B2

Reaction notes

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