Triethylamine → HCID 66628311, compound

HRID 1046842Notes

Reaction equation

HRID 1046842 reaction equation
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[CH2:13]([O:20][C:21](=[O:53])[NH:22][C:23]1[N:52]=[C:26]2[N:27]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:50])[F:49])[CH:43]=3)[C:28]([CH3:41])=[C:29]([C:39]#[N:40])[C@@H:30]([C:31]3[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=3)[N:25]2[N:24]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1.C1COCC1>[CH2:13]([O:20][C:21](=[O:53])[N:22]([C:23]1[N:52]=[C:26]2[N:27]([C:42]3[CH:47]=[CH:46][CH:45]=[C:44]([C:48]([F:51])([F:49])[F:50])[CH:43]=3)[C:28]([CH3:41])=[C:29]([C:39]#[N:40])[C@@H:30]([C:31]3[CH:32]=[CH:33][C:34]([C:37]#[N:38])=[CH:35][CH:36]=3)[N:25]2[N:24]=1)[S:9]([CH3:8])(=[O:11])=[O:10])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70223867HCID 70223867, compound

Product 1

HCID 66628311HCID 66628311, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon protective gas and at room temperature, triethylamine (11.1 mg, 140 mmol, 2.6 eq.) and methanesulfonyl chloride (41 mg, 360 mmol, 10 eq.) were added to a solution of benzyl{(7R)-6-cyano-7-(4-cyanophenyl)-5-methyl-4-[3-(trifluoromethyl)phenyl]-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-2-yl}carbamate (20 mg, 36 mmol; Example 38) in dry pyridine (2 ml) and THF (2 ml), and the mixture was stirred for 12 h. The reaction mixture was then concentrated under reduced pressure and directly purified by preparative HPLC (Reprosil C18 column, 30×200 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (17.4 mg, 72% of theory).

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. customdirectly purified by preparative HPLC (Reprosil C18 column, 30×200 mm; mobile phase: acetonitrile-water-0.1% TFA)
  3. customAfter lyophilization, the product was obtained as a solid (17.4 mg, 72% of theory)

Sources & evidence

ORD record
ord-613e886043164c128b125af9269b90b8
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

Loading…