Hydrochloric Acid → HCID 86723574, compound

HRID 1754282Notes

Reaction equation

HRID 1754282 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:14]([F:15])=[CH:13][N:12]=[C:11]([C:16]([OH:18])=O)[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.Cl.[CH:20]1([N:23]2[CH:27]=[N:26][N:25]=[C:24]2[C:28]2[S:29][CH:30]=[C:31]([NH2:33])[N:32]=2)[CH2:22][CH2:21]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[C:14]([F:15])=[CH:13][N:12]=[C:11]([C:16]([NH:33][C:31]4[N:32]=[C:28]([C:24]5[N:23]([CH:20]6[CH2:22][CH2:21]6)[CH:27]=[N:26][N:25]=5)[S:29][CH:30]=4)=[O:18])[CH:10]=3)[CH:8]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58035649HCID 58035649, compoundHCID 86723572HCID 86723572, compound

Product 1

HCID 86723574HCID 86723574, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of intermediate C.HCl (340 mg, 1.2 mmol), intermediate A (261 mg, 1.26 mmol), HATU (638 mg, 1.68 mmol), and N-methyl morpholine (330 μL, 3.00 mmol) was added DMF (5 mL) and the reaction was stirred for 2 hours. The mixture was concentrated, redissolved in a minimal amount of CH3CN, and water was added dropwise until a thick slurry was formed. The solids were isolated by filtration and washed with CH3CN to afford 320 mg. M+1=437.2

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionredissolved in a minimal amount of CH3CN, and water
  3. additionwas added dropwise until a thick slurry
  4. customwas formed
  5. customThe solids were isolated by filtration
  6. washwashed with CH3CN
  7. customto afford 320 mg

Sources & evidence

ORD record
ord-f44daf80781b45f3a6d514bf0a3d5078
Source dataset
uspto-grants-2015_10
Patent number
US09169243B2

Reaction notes

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