Triethylamine → HCID 86732377, compound

HRID 517254Notes

Reaction equation

HRID 517254 reaction equation
F[B-](F)(F)F.C[N+](C)=C(N(C)C)ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.[C:30]([C:32]1[CH:37]=[CH:36][C:35]([CH:38]2[C:47]3[C:46](=[O:48])[CH2:45][CH2:44][CH2:43][C:42]=3[N:41]([C:49]3[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:58])([F:57])[F:56])[CH:50]=3)[C:40](=[O:59])[N:39]2[CH2:60][C:61]([OH:63])=O)=[CH:34][CH:33]=1)#[N:31].[CH3:64][N:65]1[C:69]2[CH2:70][NH:71][CH2:72][C:68]=2[CH:67]=[N:66]1>CN(C)C=O>[CH3:64][N:65]1[C:69]2[CH2:70][N:71]([C:61](=[O:63])[CH2:60][N:39]3[CH:38]([C:35]4[CH:34]=[CH:33][C:32]([C:30]#[N:31])=[CH:37][CH:36]=4)[C:47]4[C:46](=[O:48])[CH2:45][CH2:44][CH2:43][C:42]=4[N:41]([C:49]4[CH:54]=[CH:53][CH:52]=[C:51]([C:55]([F:57])([F:56])[F:58])[CH:50]=4)[C:40]3=[O:59])[CH2:72][C:68]=2[CH:67]=[N:66]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 108780601-Methyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazoleHCID 86732371HCID 86732371, compound

Product 1

HCID 86732377HCID 86732377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N,N′,N′-Tetramethyl-O-(benzotriazol-1-yl)uronium tetrafluoroborate (161 mg, 0.50 mmol) and triethylamine (210 μL, 1.51 mmol) are added to a mixture of 2-(4-(4-cyanophenyl)-2,5-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazolin-3(4H)-yl)acetic acid (example 32, 235 mg, 0.50 mmol) in N,N-dimethylform-amide (2 mL). After 5 min a solution of 1-methyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole (123 mg, 1.00 mmol) in N,N-dimethylformamide (3 mL) is added, and the mixture is stirred over night and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 86 mg; ESI mass spectrum [M+H]+=575; Retention time HPLC: 0.86 min (Z011_S03).

Workup

  1. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom0.86 min (Z011_S03)

Sources & evidence

ORD record
ord-89e0cf87c80f48f8a9a87bd5de0b0389
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

Loading…