Triethylamine → HCID 178446149, compound

HRID 2368599Notes

Reaction equation

HRID 2368599 reaction equation
[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([OH:17])=O)[O:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18]([N:23]1[C:31]2[N:30]=[C:29]([C:32]([F:35])([F:34])[F:33])[NH:28][C:27]=2[C:26](=[O:36])[NH:25]/[C:24]/1=[N:37]\[NH2:38])[CH2:19][CH2:20][CH2:21][CH3:22].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.CCOC(C)=O>[CH2:1]([C:8]1[N:12]=[C:11]([CH2:13][CH2:14][C:15]([NH:38]/[N:37]=[C:24]2\[NH:25][C:26](=[O:36])[C:27]3[NH:28][C:29]([C:32]([F:35])([F:34])[F:33])=[N:30][C:31]=3[N:23]\2[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[O:17])[O:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 398703933-(3-Benzyl-1,2,4-oxadiazol-5-yl)propanoic acidHCID 178446162HCID 178446162, compound

Product 1

HCID 178446149HCID 178446149, compoundYield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The mixture of 3-(3-benzyl-1,2,4-oxadiazol-5-yl)propanoic acid (100.0 mg, 0.431 mmole), (2E)-3-pentyl-8-(trifluoromethyl)-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (144.1 mg, 0.474 mmole), BOP (209.5 mg, 0.474 mmole) and triethylamine (0.120 ml, 0.861 mmole). in DMF (4 ml) was stirred at room temperature overnight. The mixture was diluted with EtOAc (100 ml) and washed with water, then brine. The organic phase was dried over Na2SO4, filtrated and concentrated to give the desired product (220.1 mg, 98.6%) as yellowish oil. LCMS calculated for C23H26F3N8O3 (M+H): m/z=5192. Found 519.2.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltrated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b9aac5e2c1849899338ddfb903a8d2e
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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