1,1'-Carbonyldiimidazole → HCID 25001766, compound

HRID 658998Notes

Reaction equation

HRID 658998 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[F:13][C:14]([F:24])([F:23])[O:15][C:16]1[CH:17]=[C:18](C=C[CH:22]=1)N.NC1C=[CH:42][C:29]([O:30][C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH2:38][CH2:39][CH2:40][OH:41])[N:32]=2)=[CH:28][CH:27]=1>ClCCl>[OH:41][CH2:40][CH2:39][CH2:38][NH:37][C:33]1[N:32]=[C:31]([O:30][C:29]2[CH:42]=[CH:11][C:12]([NH:8][C:1]([NH:3][C:7]3[CH:6]=[CH:22][C:16]([O:15][C:14]([F:13])([F:23])[F:24])=[CH:17][CH:18]=3)=[O:2])=[CH:27][CH:28]=2)[CH:36]=[CH:35][N:34]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 737533-(Trifluoromethoxy)anilineHCID 67524085HCID 67524085, compound

Product 1

HCID 25001766HCID 25001766, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

180 mg (1.11 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 179 mg (1.01 mmol) 3-trifluoromethoxyaniline in 4.0 ml dichloromethane and stirred for 12 h. A solution of 263 mg (1.01 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 6.0 ml dichloromethane was added within 30 min. and the mixture stirred for 12 h at r.t. The reaction mixture was filtered, the filtrate evaporated and the residue purified by chromatography on silica gel (dichloromethane/methanol 95:5). The obtained material was washed with dichloromethane, the precipitate was isolated by filtration and dried. Yield: 160 mg (34%) of the title compound.

Workup

  1. stirringthe mixture stirred for 12 h at r.t
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate evaporated
  4. customthe residue purified by chromatography on silica gel (dichloromethane/methanol 95:5)
  5. washThe obtained material was washed with dichloromethane
  6. customthe precipitate was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-8e3a2802643f464a8d4fd1ed77629986
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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