Ethanolamine → HCID 46841342, compound

HRID 2200981Notes

Reaction equation

HRID 2200981 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.C(N(CC)CC)C.[C:21]([C:23]1[C@@H:28]([C:29]2[CH:34]=[CH:33][C:32]([C:35]#[N:36])=[CH:31][CH:30]=2)[N:27]2[N:37]=[C:38]([NH:40][C:41](=[O:50])OCC3C=CC=CC=3)[N:39]=[C:26]2[N:25]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=2)[C:24]=1[CH3:61])#[N:22].[NH2:62][CH2:63][CH2:64][OH:65]>CN(C1C=CN=CC=1)C.ClCCl>[C:21]([C:23]1[C@@H:28]([C:29]2[CH:30]=[CH:31][C:32]([C:35]#[N:36])=[CH:33][CH:34]=2)[N:27]2[N:37]=[C:38]([NH:40][C:41]([NH:62][CH2:63][CH2:64][OH:65])=[O:50])[N:39]=[C:26]2[N:25]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:58])([F:60])[F:59])[CH:52]=2)[C:24]=1[CH3:61])#[N:22]

Participants

7

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 70223867HCID 70223867, compound

Product 1

HCID 46841342HCID 46841342, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

Under an atmosphere of argon protective gas and at 0° C., 4-nitrophenyl chloroformate (7.3 mg, 36 μmol, 2 eq.), triethylamine (3.1 mg, 40 μmol, 2.2 eq.) and DMAP (0.2 mg, 1.8 μmol, 0.1 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 (10 mg, 18 μmol) in dry dichloromethane (1 ml), and the mixture was stirred at 4° C. for 12 h. At 0° C., 2-aminoethanol (8.5 mg, 139 μmol, 10 eq.) was then added, and the mixture was once more stirred at 4° C. for 12 h. The reaction mixture was then concentrated under reduced pressure and purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (1.9 mg, 27% of theory).

Workup

  1. stirringthe mixture was once more stirred at 4° C. for 12 h
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. custompurified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (1.9 mg, 27% of theory)

Sources & evidence

ORD record
ord-0c2f16df53684ae2afe31bdded8c839f
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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