Ethanolamine → HCID 46841342, compound

HRID 1046881Notes

Reaction equation

HRID 1046881 reaction equation
ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.C(N(CC)CC)C.C(O[C:29](=[O:61])[NH:30][C:31]1[N:60]=[C:34]2[N:35]([C:50]3[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:59])([F:58])[F:57])[CH:51]=3)[C:36]([CH3:49])=[C:37]([C:47]#[N:48])[C@@H:38]([C:39]3[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=3)[N:33]2[N:32]=1)C1C=CC=CC=1.[NH2:62][CH2:63][CH2:64][OH:65]>CN(C1C=CN=CC=1)C.ClCCl>[C:47]([C:37]1[C@@H:38]([C:39]2[CH:44]=[CH:43][C:42]([C:45]#[N:46])=[CH:41][CH:40]=2)[N:33]2[N:32]=[C:31]([NH:30][C:29]([NH:62][CH2:63][CH2:64][OH:65])=[O:61])[N:60]=[C:34]2[N:35]([C:50]2[CH:55]=[CH:54][CH:53]=[C:52]([C:56]([F:57])([F:59])[F:58])[CH:51]=2)[C:36]=1[CH3:49])#[N:48]

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-a33463a6f5564c51a5fdcccc0db27ffe
Source dataset
uspto-grants-2013_10
Patent number
US08569314B2

Reaction notes

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