Ammonia → HCID 86732376, compound

HRID 517253Notes

Reaction equation

HRID 517253 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[C:49]3[C:48](=[O:50])[CH2:47][CH2:46][CH2:45][C:44]=3[N:43]([C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:60])([F:59])[F:58])[CH:52]=3)[C:42](=[O:61])[N:41]2[CH2:62][C:63](O)=[O:64])=[CH:36][CH:35]=1)#[N:33].N>CN(C)C=O>[C:32]([C:34]1[CH:39]=[CH:38][C:37]([CH:40]2[C:49]3[C:48](=[O:50])[CH2:47][CH2:46][CH2:45][C:44]=3[N:43]([C:51]3[CH:56]=[CH:55][CH:54]=[C:53]([C:57]([F:59])([F:60])[F:58])[CH:52]=3)[C:42](=[O:61])[N:41]2[CH2:62][C:63]([NH2:8])=[O:64])=[CH:36][CH:35]=1)#[N:33]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86732371HCID 86732371, compound

Product 1

HCID 86732376HCID 86732376, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (38 mg, 100 μmol) and triethylamine (70 μL, 500 μmol) 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)acetic acid (example 32, 47 mg, 100 μmol) in N,N-dimethylformamide (0.5 mL). After 20 min ammonia (0.5 M in 1,4-dioxane, 200 μL, 100 μmol) is added, and the mixture is stirred at room temperature for 2 h and purified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3). Yield: 29 mg; ESI mass spectrum [M+H]+=469; Retention time HPLC: 0.84 min (Z018_S04).

Workup

  1. custompurified by preparative HPLC (Waters Xbridge™-C18, gradient of acetonitrile in water, 0.1% NH3)
  2. custom0.84 min (Z018_S04)

Sources & evidence

ORD record
ord-681e3f04d05c409d83d9492521166f21
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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