Ammonia → HCID 66628688, compound

HRID 2200990Notes

Reaction equation

HRID 2200990 reaction equation
C[N:2](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[C:32]([C:34]1[C@@H:39]([C:40]2[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=2)[N:38]2[N:48]=[C:49]([NH:51][CH2:52][C:53](O)=[O:54])[N:50]=[C:37]2[N:36]([C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:64])[F:63])[CH:57]=2)[C:35]=1[CH3:66])#[N:33].N.O1CCOCC1>CN(C=O)C>[C:32]([C:34]1[C@@H:39]([C:40]2[CH:45]=[CH:44][C:43]([C:46]#[N:47])=[CH:42][CH:41]=2)[N:38]2[N:48]=[C:49]([NH:51][CH2:52][C:53]([NH2:2])=[O:54])[N:50]=[C:37]2[N:36]([C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([C:62]([F:65])([F:63])[F:64])[CH:57]=2)[C:35]=1[CH3:66])#[N:33]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66628192HCID 66628192, compound

Product 1

HCID 66628688HCID 66628688, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Under an atmosphere of argon protective gas and at 0° C., HATU (25 mg, 66 μmol, 3 eq.) and triethylamine (11 mg, 110 μmol, 5 eq.) were added to a solution of N-{(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}glycine (10.5 mg, 22 μmol) in DMF (1 ml). After the reaction mixture has thawed to RT, it was once more cooled to 0° C., and a 0.5 M solution of ammonia in dioxane (0.44 ml, 219 μmol, 10 eq.) was then added. The mixture was stirred for 2 h, during which time it gradually warmed to RT. The reaction mixture was then concentrated under reduced pressure and the residue was purified by preparative HPLC (Kromasil C18 column, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (9.2 mg, 88% of theory).

Workup

  1. customhas thawed to RT
  2. temperaturegradually warmed to RT
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. customthe residue was purified by preparative HPLC (Kromasil C18 column, 50×20 mm; mobile phase: acetonitrile-water-0.1% TFA)
  5. customAfter lyophilization, the product was obtained as a solid (9.2 mg, 88% of theory)

Sources & evidence

ORD record
ord-d43bbed047ad498ebc245db62556e6a1
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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