4-Methylmorpholine → (S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(2-(4-(1,1,1-trifluoropropan-2-yl)-4H-1,2,4-triazol-3-yl)thiazol-4-yl)picolinamide

HRID 2091626Notes

Reaction equation

HRID 2091626 reaction equation
[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([OH:17])=O)[CH:10]=3)[CH:8]=2)[CH2:3][CH2:2]1.[F:18][C:19]([F:34])([F:33])[C@@H:20]([N:22]1[CH:26]=[N:25][N:24]=[C:23]1[C:27]1[S:28][CH:29]=[C:30]([NH2:32])[N:31]=1)[CH3:21].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>CN(C)C=O>[CH:1]1([C:4]2[N:5]=[CH:6][N:7]([C:9]3[CH:14]=[CH:13][N:12]=[C:11]([C:15]([NH:32][C:30]4[N:31]=[C:27]([C:23]5[N:22]([C@@H:20]([CH3:21])[C:19]([F:34])([F:33])[F:18])[CH:26]=[N:25][N:24]=5)[S:28][CH:29]=4)=[O:17])[CH:10]=3)[CH:8]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 580356504-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acidHCID 66628937(S)-2-(4-(1,1,1-trifluoropropan-2-yl)-4H-1,2,4-triazol-3-yl)thiazol-4-amine

Product 1

HCID 66628787(S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(2-(4-(1,1,1-trifluoropropan-2-yl)-4H-1,2,4-triazol-3-yl)thiazol-4-yl)picolinamideYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-cyclopropyl-1H-imidazol-1-yl)picolinic acid (50 mg, 0.218 mmol), (S)-2-(4-(1,1,1-trifluoropropan-2-yl)-4H-1,2,4-triazol-3-yl)thiazol-4-amine (53 mg, 0.208 mmol), HATU (99 mg, 0.262 mmol), and N-methylmorpholine (30 μL, 0.262 mmol) in N,N-dimethylformamide (1 mL) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure, the residue was suspended in acetonitrile/water and the solids were isolated by filtration, washed with water (2 mL), acetonitrile (2 mL) and diethyl ether (5 mL) and dried under vacuum to afford (S)-4-(4-cyclopropyl-1H-imidazol-1-yl)-N-(2-(4-(1,1,1-trifluoropropan-2-yl)-4H-1,2,4-triazol-3-yl)thiazol-4-yl)picolinamide as a white powder (69 mg, 71% yield).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe solids were isolated by filtration
  3. washwashed with water (2 mL), acetonitrile (2 mL) and diethyl ether (5 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-095dec9fe4c94fb2b22d8bc29ae47c3e
Source dataset
uspto-grants-2013_05
Patent number
US08440665B2

Reaction notes

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