Tert-Butylamine → HCID 24993815, compound

HRID 1947442Notes

Reaction equation

HRID 1947442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[CH:14][C:13]([C:16]([OH:18])=O)=[CH:12][N:11]3[CH:19]=2)=[CH:4][CH:3]=1.[C:20]([NH2:24])([CH3:23])([CH3:22])[CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>CN(C=O)C>[C:20]([NH:24][C:16]([C:13]1[CH:14]=[CH:15][C:10]2[N:11]([CH:19]=[C:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[N:9]=2)[CH:12]=1)=[O:18])([CH3:23])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 1485634HCID 1485634, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 24993815HCID 24993815, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluoro-phenyl)-imidazo[1,2-a]pyridine-6-carboxylic acid (example 45; 40 mg, 0.14 mmol), tert-butylamine (73.1 mg, 0.0.27 mmol), HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate; 57.2 mg, 0.15 mmol) and triethylamine (56.8 μl, 0.41 mmol) in 3 ml DMF were stirred at room temperature for 2 hours. The mixture was evaporated. ethyl acetate and water were added, the organic layer was separated, washed with water, dried and evaporated. The crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA) to yield 44 mg (99%) of the desired product. MS: M+H+=312.15.

Workup

  1. customThe mixture was evaporated
  2. additionethyl acetate and water were added
  3. customthe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (RP18, acetonitrile/water 0.1% TFA)

Sources & evidence

ORD record
ord-79484eb8c73e4348a1e956e215f0f0d5
Source dataset
uspto-grants-2013_03
Patent number
US08399476B2

Reaction notes

Loading…