Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 178481759, compound

HRID 246618Notes

Reaction equation

HRID 246618 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[N:8]=[C:7]2[C:14]1[N:15]=[C:16]2[C:22]([C:23](O)=[O:24])=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1.[NH2:27][C@@H:28]1[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:40])([CH3:39])[CH3:38])[CH2:30][CH2:29]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[F:1][CH:2]([F:26])[O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:13])[N:8]=[C:7]2[C:14]1[N:15]=[C:16]2[C:22]([C:23]([NH:27][C@@H:28]3[CH2:33][CH2:32][C@H:31]([NH:34][C:35](=[O:41])[O:36][C:37]([CH3:39])([CH3:38])[CH3:40])[CH2:30][CH2:29]3)=[O:24])=[CH:21][NH:20][C:17]2=[N:18][CH:19]=1

Participants

5

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 712795422-(5-(Difluoromethoxy)-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acidHCID 178418966HCID 178418966, compound

Product 1

HCID 178481759HCID 178481759, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(5-(Difluoromethoxy)-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.43 mmol), tert-butyl cis-4-aminocyclohexylcarbamate (102 mg, 0.48 mmol) and HATU (196 mg, 0.51 mmol) in 15 mL of dry THF was stirred for 4 hours. The reaction mixture was evaporated to dryness, the residue was suspended in 50 mL of 0.5N HCl, extracted with ethyl acetate (3×50 mL), dried over sodium sulfate and concentrated to give tert-butyl cis-4-(2-(5-(difluoromethoxy)-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)cyclohexylcarbamate (54 mg, crude). LCMS: (M+H)+=556; (M+Na)+=578. Used in the next step without further purification.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e48d0e6553d9451a9dae8d2245d51c01
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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