3-(Trifluoromethyl)phenyl isocyanate → 1-(3-(8-(Pyridin-4-ylmethylamino)imidazo[1,2-a]pyrazin-6-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea

HRID 854445Notes

Reaction equation

HRID 854445 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=2)[CH:5]=[CH:6][CH:7]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29]([N:33]=[C:34]=[O:35])[CH:30]=[CH:31][CH:32]=1>C1(C)C=CC=CC=1>[N:22]1[CH:23]=[CH:24][C:19]([CH2:18][NH:17][C:10]2[C:11]3[N:12]([CH:14]=[CH:15][N:16]=3)[CH:13]=[C:8]([C:4]3[CH:3]=[C:2]([NH:1][C:34]([NH:33][C:29]4[CH:30]=[CH:31][CH:32]=[C:27]([C:26]([F:25])([F:36])[F:37])[CH:28]=4)=[O:35])[CH:7]=[CH:6][CH:5]=3)[N:9]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 58934056[6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-pyridin-4-ylmethyl-amine

Product 1

HCID 117558121-(3-(8-(Pyridin-4-ylmethylamino)imidazo[1,2-a]pyrazin-6-yl)phenyl)-3-(3-(trifluoromethyl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1.00 eq. of [6-(3-Amino-phenyl)-imidazo[1,2-a]pyrazin-8-yl]-pyridin-4-ylmethyl-amine (5) and 1.00 eq. of 3-trifluoromethylphenyl isocyanate in toluene is stirred at room temperature for 24 hrs. The mixture is partitioned between EtOAc and saturated NaHCO3. The aqueous phase is extracted with EtOAc and the combined extracts are dried over Na2SO4. The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography (EtOAc) to yield 1-(3-{8-[(Pyridin-4-ylmethyl)-amino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-3-(3-trifluoromethyl-phenyl)-urea 6. MF═C26H20F3N7O, MW=503.48; Mass Spec m/z (M++1) 504.17.

Workup

  1. customThe mixture is partitioned between EtOAc and saturated NaHCO3
  2. extractionThe aqueous phase is extracted with EtOAc
  3. dry with materialthe combined extracts are dried over Na2SO4
  4. customThe solvent is removed under reduced pressure
  5. customthe resulting residue is purified by flash chromatography (EtOAc)

Sources & evidence

ORD record
ord-005d68a20e4a474db620eb6156e3dd8b
Source dataset
uspto-grants-2007_08
Patent number
US07259164B2

Reaction notes

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