Tert-Butylamine → HCID 71279911, compound

HRID 246630Notes

Reaction equation

HRID 246630 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[N:16]=[C:15]3[C:17]([C:20](O)=[O:21])=[CH:18][NH:19][C:14]3=[N:13][CH:12]=2)=[N:3]1.[C:23]([NH2:27])([CH3:26])([CH3:25])[CH3:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[C:23]([NH:27][C:20]([C:17]1[C:15]2[C:14](=[N:13][CH:12]=[C:11]([C:4]3[C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[N:2]([CH3:1])[N:3]=3)[N:16]=2)[NH:19][CH:18]=1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71280375HCID 71280375, compound

Product 1

HCID 71279911HCID 71279911, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(1-Methyl-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxylic acid (120 mg, 0.41 mmol), tert-butylamine (0.1 mL, 0.9 mmol) and HATU (233 mg, 0.61 mmol) in 20 mL of dry THF was stirred for 4 hours. The reaction mixture was evaporated to dryness, 20 mL of 0.5N HCl were added to the residue, product extracted with ethyl acetate (3×50 mL), combined organics dried over sodium sulfate and concentrated. The residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with ethyl acetate/petroleum ether=2:1) to give N-tert-butyl-2-(1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (47 mg, 33.7%). LCMS: (M+H)+=349; 1H NMR (300 MHz, DMSO): δ 12.75 (s, 1H), 9.07 (s, 1H), 8.48 (d, 1H, J=7.8 Hz), 8.35 (s, 1H), 7.96 (s, 1H), 7.5 (d, 1H, J=7.8 Hz), 7.49 (t, 1H, J=7.5 Hz), 7.27-7.22 (m, 1H), 4.17 (s, 3H), 1.52 (s, 9H).

Workup

  1. customThe reaction mixture was evaporated to dryness, 20 mL of 0.5N HCl
  2. additionwere added to the residue, product
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. dry with materialcombined organics dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica gel, 200-300 mesh, eluting with ethyl acetate/petroleum ether=2:1)

Sources & evidence

ORD record
ord-26021a2ee4554f0ea85fa1de38872d11
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…