Diisopropylethylamine → N-(4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-yl)-2-[2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetamide

HRID 1446765Notes

Reaction equation

HRID 1446765 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[C:8]([C:10]2[N:14]3[CH:15]=[CH:16][C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)=[CH:18][C:13]3=[N:12][CH:11]=2)[CH:7]=[CH:6][C:5]=1[CH2:25][C:26](O)=[O:27].[C:29]([C:33]1[CH:38]=[C:37]([CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:36]=[C:35]([NH2:46])[CH:34]=1)([CH3:32])([CH3:31])[CH3:30].C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C(OCC)(=O)C>[C:29]([C:33]1[CH:38]=[C:37]([CH2:39][N:40]2[CH2:45][CH2:44][O:43][CH2:42][CH2:41]2)[N:36]=[C:35]([NH:46][C:26](=[O:27])[CH2:25][C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:14]4[CH:15]=[CH:16][C:17]([C:19]5[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=5)=[CH:18][C:13]4=[N:12][CH:11]=3)=[CH:9][C:4]=2[F:3])[CH:34]=1)([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68543260[2-Fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetic acid dihydrochlorideHCID 685448704-tert-Butyl-6-morpholin-4-ylmethyl-pyridin-2-ylamine

Product 1

HCID 57863418N-(4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-yl)-2-[2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetamideYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve [2-fluoro-4-(7-pyridin-4-yl-imidazo[1,2-a]pyridin-3-yl)-phenyl]-acetic acid dihydrochloride (6.24 g, 14.84 mmol) and 4-tert-butyl-6-morpholin-4-ylmethyl-pyridin-2-ylamine (3.70 g, 14.84 mmol) in anhydrous DMF (40 mL). Add diisopropyl-ethylamine (8.5 mL, 48.97 mmol) and HATU (6.21 g, 16.32 mmol). Stir the reaction mixture at room temperature for 40 minutes. Dilute with ethyl acetate (800 mL). Wash with aqueous saturated sodium chloride (3×100 mL), sodium bicarbonate (sat. 3×100 mL), water (3×100 mL). Dry the organic layer over magnesium sulfate, filter off the drying reagent, and concentrate to oil. Chromatograph the crude product on silica (0-4% 2 M ammonia methanol/dichloro-methane). Recrystallize from dichloromethane/ether/hexane to provide the title compound 5.50 g (9.5 mmol, 64%) white solid as product. MS (ES), m/z 579 (M+1).

Workup

  1. washWash with aqueous saturated sodium chloride (3×100 mL), sodium bicarbonate (sat. 3×100 mL), water (3×100 mL)
  2. dry with materialDry the organic layer over magnesium sulfate
  3. filtrationfilter off the drying reagent
  4. concentrationconcentrate to oil
  5. customRecrystallize from dichloromethane/ether/hexane

Sources & evidence

ORD record
ord-d6b13e6d309e42a8bee7af147b6f1603
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

Loading…