Triethylamine → HCID 73053317, compound

HRID 1497822Notes

Reaction equation

HRID 1497822 reaction equation
[NH2:1][C:2]1[N:24]=[C:5]2[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)=[C:7]([CH3:13])[C:8]([C:10](O)=O)=[CH:9][N:4]2[N:3]=1.C(OC([NH:32][C:33](=[NH:36])SC)=O)(C)(C)C.[CH2:37](N(CC)CC)[CH3:38].CN(C(O[N:52]1[N:60]=N[C:54]2[CH:55]=[CH:56][CH:57]=[N:58][C:53]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)Cl>[NH2:36][C:33]1[N:32]=[C:10]([C:8]2[C:7]([CH3:13])=[C:6]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:22])([F:23])[F:21])[CH:15]=3)[C:5]3[N:4]([N:3]=[C:2]([NH2:1])[N:24]=3)[CH:9]=2)[N:52]([C:53]2[CH:54]=[CH:55][C:56]([C:57]#[N:58])=[CH:38][CH:37]=2)[N:60]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86708121HCID 86708121, compoundHCID 137319820tert-butyl N-[(methylsulfanyl)methanimidoyl]carbamate

Product 1

HCID 73053317HCID 73053317, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine-6-carboxylic acid (Int. 36, 246 mg, 0.732 mmol) and N-(tert-butyloxycarbonyl)-S-methylisothiourea (139 mg, 0.732 mmol) in THF (5 mL) were treated with triethylamine (306 μL, 2.196 mmol) and HATU (384 mg, 1.098 mmol) and then the reaction mixture was heated at 80° C. for 1.5 hrs. The reaction mixture was treated with saturated aqueous NaHCO3 solution (20 mL) and DCM (20 mL) and the organic phase was separated and concentrated in vacuo. The resulting material was purified by chromatography on silica eluting with a gradient of 0-10% MeOH in DCM to give the title compound as a white solid (348 mg).

Workup

  1. customthe organic phase was separated
  2. concentrationconcentrated in vacuo
  3. customThe resulting material was purified by chromatography on silica eluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-36ddc3970d95400fa0606320a0155ea9
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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