Ethanolamine → USRE47493, Example 61

HRID 517274Notes

Reaction equation

HRID 517274 reaction equation
C(N(CC)CC)C.[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[N:19]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=3)[C:18](=[O:37])[N:17]2[CH:38]([CH3:42])[C:39]([OH:41])=O)=[CH:12][CH:11]=1)#[N:9].F[B-](F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.[CH2:65]([CH2:67][NH2:68])[OH:66]>CN(C)C=O>[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[C:25]3[C:24](=[O:26])[CH2:23][CH2:22][CH2:21][C:20]=3[N:19]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:36])[F:34])[CH:28]=3)[C:18](=[O:37])[N:17]2[CH:38]([CH3:42])[C:39]([NH:68][CH2:67][CH2:65][OH:66])=[O:41])=[CH:12][CH:11]=1)#[N:9]

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 867323492-(4-(4-Cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)propanoic acid2×

Product 1

HCID 86732399USRE47493, Example 61

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Triethylamine (55 μL, 0.40 mmol) is added to a solution of 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)-propanoic acid (intermediate 59, 50 mg, 0.10 mmol) in N,N-dimethylformamide, and the mixture is stirred for 10 min at room temperature. N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (33 mg, 0.10 mmol) is added, and the mixture is stirred for 15 min. Ethanolamine (15 μL, 0.25 mml) is added, and the mixture is stirred for 1 h, diluted with N,N-dimethylformamide and purified by preparative HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 39 mg; ESI mass spectrum [M+H]+=527; Retention time HPLC: 0.86 min (Z018_S04).

Workup

  1. stirringthe mixture is stirred for 15 min
  2. stirringthe mixture is stirred for 1 h
  3. custompurified by preparative HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  4. custom0.86 min (Z018_S04)

Sources & evidence

ORD record
ord-30e7d309be1748f199e05895157a897e
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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