4-Methylmorpholine → N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide

HRID 715806Notes

Reaction equation

HRID 715806 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][CH:10]([C:13]3[S:14][C:15]([C:18]([O-:20])=O)=[CH:16][N:17]=3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[N:22]1[CH:23]=[CH:24][N:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][C:26]=12.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[N:22]1[CH:23]=[CH:24][N:25]2[CH:30]=[CH:29][C:28]([CH2:31][NH:32][C:18]([C:15]3[S:14][C:13]([CH:10]4[CH2:9][CH2:8][N:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH2:12][CH2:11]4)=[N:17][CH:16]=3)=[O:20])=[CH:27][C:26]=12

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 55289825Imidazo(1,2-a)pyridin-7-ylmethanamineHCID 86701985Lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate

Product 1

HCID 86701987N-(imidazo[1,2-a]pyridin-7-ylmethyl)-2-(1-phenylpiperidin-4-yl)-1,3-thiazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Lithium 2-(1-phenylpiperidin-4-yl)thiazole-5-carboxylate (28.8 mg, 0.098 mmol), imidazo[1,2-a]pyridin-7-ylmethanamine (17.31 mg, 0.118 mmol), 4-methylmorpholine (49.6 mg, 0.490 mmol) and 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (55.9 mg, 0.147 mmol) were combined in a vial with dichloromethane (2.5 ml) and the reaction was stirred overnight. The mixture was partitioned between dichloromethane and saturated sodium bicarbonate. The organic layers were dried with sodium sulfate, filtered, and concentrated. Trituration of the crude material with dichloromethane provided the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.21 (t, J=5.9 Hz, 1H), 8.49 (dd, J=7.0, 0.9 Hz, 1H), 8.34 (s, 1H), 7.91-7.88 (m, 1H), 7.52 (d, J=1.2 Hz, 1H), 7.43-7.38 (m, 1H), 7.26-7.16 (m, 2H), 7.01-6.93 (m, 2H), 6.84 (dd, J=7.0, 1.7 Hz, 1H), 6.81-6.72 (m, 1H), 4.48 (d, J=5.9 Hz, 2H), 3.81-3.73 (m, 2H), 3.24-3.01 (m, 1H), 2.90-2.78 (m, 2H), 2.19-2.09 (m, 2H), 1.90-1.73 (m, 2H); MS (ESI(+)) m/e 418 (M+H)+.

Workup

  1. customThe mixture was partitioned between dichloromethane and saturated sodium bicarbonate
  2. dry with materialThe organic layers were dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-83249458d53440778ad621bb34bccc5b
Source dataset
uspto-grants-2015_11
Patent number
US09187472B2

Reaction notes

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