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 1423344Notes

Reaction equation

HRID 1423344 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-ff91bb2f7ff342488b4cc6b4f8f4a353
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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