1,1'-Carbonyldiimidazole → HCID 67523892, compound

HRID 659036Notes

Reaction equation

HRID 659036 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[C:13]1([O:19][C:20]([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=C(N)C=3)[C:24]([CH3:33])([CH3:32])[CH2:23]2)=[O:21])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.NC1C=[CH:51][C:38]([O:39][C:40]2[CH:45]=[CH:44][N:43]=[C:42]([NH:46][CH2:47][CH2:48][CH2:49][OH:50])[N:41]=2)=[CH:37][CH:36]=1>C1COCC1>[C:13]1([O:19][C:20]([N:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:12]([NH:8][C:1]([NH:3][C:7]4[CH:6]=[CH:51][C:38]([O:39][C:40]5[CH:45]=[CH:44][N:43]=[C:42]([NH:46][CH2:47][CH2:48][CH2:49][OH:50])[N:41]=5)=[CH:37][CH:36]=4)=[O:2])[CH:11]=3)[C:24]([CH3:32])([CH3:33])[CH2:23]2)=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 67523918HCID 67523918, compoundHCID 67524085HCID 67524085, compound

Product 1

HCID 67523892HCID 67523892, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

278 mg (1.71 mmol) 1,1′-Carbonyl-diimidazol (CDI) were given to a solution of 484 mg (1.63 mmol) 6-amino-3,3-dimethyl-2,3-dihydro-indole-1-carboxylic acid phenyl ester in 10 ml THF. A solution of 425 mg (1.63 mmol) 3-[4-(4-Amino-phenoxy)-pyrimidin-2-ylamino]-propan-1-ol in 10 ml THF was added within 15 min. and the mixture stirred for 12 h at r.t. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/methanol 95:5). The obtained material was washed with dichloromethane/ether, the precipitate was isolated by filtration and dried. Yield: 540 mg (57%) of the title compound.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified by chromatography on silica gel (dichloromethane/methanol 95:5)
  3. washThe obtained material was washed with dichloromethane/ether
  4. customthe precipitate was isolated by filtration
  5. customdried

Sources & evidence

ORD record
ord-ae711acf135748faa1227d8992c3b106
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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