4-Tert-Butylaniline → N-(4-tert-Butyl-phenyl)-3-{8-[4-(morpholine-4-carbonyl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-benzamide

HRID 751589Notes

Reaction equation

HRID 751589 reaction equation
[N:1]1([C:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16]3[C:17]4[N:18]([CH:31]=[CH:32][N:33]=4)[CH:19]=[C:20]([C:22]4[CH:23]=[C:24]([CH:28]=[CH:29][CH:30]=4)[C:25]([OH:27])=O)[N:21]=3)=[CH:11][CH:10]=2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[C:70]([C:74]1[CH:79]=[CH:78][C:77]([NH2:80])=[CH:76][CH:75]=1)([CH3:73])([CH3:72])[CH3:71]>CN(C=O)C>[C:70]([C:74]1[CH:75]=[CH:76][C:77]([NH:80][C:25](=[O:27])[C:24]2[CH:28]=[CH:29][CH:30]=[C:22]([C:20]3[N:21]=[C:16]([NH:15][C:12]4[CH:13]=[CH:14][C:9]([C:7]([N:1]5[CH2:2][CH2:3][O:4][CH2:5][CH2:6]5)=[O:8])=[CH:10][CH:11]=4)[C:17]4[N:18]([CH:31]=[CH:32][N:33]=4)[CH:19]=3)[CH:23]=2)=[CH:78][CH:79]=1)([CH3:73])([CH3:71])[CH3:72]

Participants

6

Reactant 4

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 597546943-{8-[4-(Morpholine-4-carbonyl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-benzoic acid

Product 1

HCID 11713941N-(4-tert-Butyl-phenyl)-3-{8-[4-(morpholine-4-carbonyl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-benzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-{8-[4-(Morpholine-4-carbonyl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-benzoic acid (9) (0.23 mmol), benzotriazol-1-yloxy-tris(dimethylamino)-phosphonium hexafluorophosphate reagent (0.23 mmol) and N,N′-diisopropylethylamine (0.77 mmol) is stirred under N2 for 15 min. in 1 mL DMF. 4-tert-Butyl-phenylamine (0.37 mmol) is added and the reaction stirred at rt for 8 hrs. The reaction is partitioned between ethyl acetate (15 mL) and water (15 mL) and the ethyl acetate layer washed with water (2×15 mL) and brine (1×15 mL). The organic layer is dried over sodium sulfate and the solvent removed in vacuo. The resulting crude oil is dissolved in 1 ml CH2Cl2 and clean yellow solid is precipitated by slow addition of diethyl ether, yielding the final product, (10) N-(4-tert-Butyl-phenyl)-3-{8-[4-(morpholine-4-carbonyl)-phenylamino]-imidazo[1,2-a]pyrazin-6-yl}-benzamide.

Workup

  1. customThe reaction is partitioned between ethyl acetate (15 mL) and water (15 mL)
  2. washthe ethyl acetate layer washed with water (2×15 mL) and brine (1×15 mL)
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. customthe solvent removed in vacuo
  5. dissolutionThe resulting crude oil is dissolved in 1 ml CH2Cl2
  6. customclean yellow solid is precipitated by slow addition of diethyl ether

Sources & evidence

ORD record
ord-c88490a3c3f44638ac751e6ba670ba13
Source dataset
uspto-grants-2008_07
Patent number
US07405295B2

Reaction notes

Loading…