Phenol → HCID 9958156, compound

HRID 983881Notes

Reaction equation

HRID 983881 reaction equation
O([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:32]=[CH:31][C:21]([CH2:22][N:23]4[CH2:28][CH:27]5[CH:25]([CH:26]5[CH2:29][OH:30])[CH2:24]4)=[CH:20][CH:19]=3)[CH:16]=2)[N:11]=[CH:10][N:9]=1)C1C=CC=CC=1.[CH:33]1([CH2:36][N:37]2[C:45]3[C:40](=[CH:41][C:42]([NH2:46])=[CH:43][CH:44]=3)[CH:39]=[CH:38]2)[CH2:35][CH2:34]1.Cl.[NH+]1C=CC=CC=1.C1(O)C=CC=CC=1>C(Cl)(Cl)Cl>[CH:33]1([CH2:36][N:37]2[C:45]3[C:40](=[CH:41][C:42]([NH:46][C:8]4[C:17]5[C:12](=[CH:13][CH:14]=[C:15]([C:18]6[CH:19]=[CH:20][C:21]([CH2:22][N:23]7[CH2:28][CH:27]8[CH:25]([CH:26]8[CH2:29][OH:30])[CH2:24]7)=[CH:31][CH:32]=6)[CH:16]=5)[N:11]=[CH:10][N:9]=4)=[CH:43][CH:44]=3)[CH:39]=[CH:38]2)[CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 996PhenolHCID 15450141HCID 15450141, compoundHCID 154501461-(Cyclopropylmethyl)-1H-indol-5-amineHCID 21584435Pyridinium hydrochloride

Product 1

HCID 9958156HCID 9958156, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
110 °C

Procedure

To a 3 mL Wheaton vial was added {3-[4-(4-phenoxy-quinazolin-6-yl)-benzyl}-3-aza-bicyclo[3.1.0]hex-6-yl)-methanol 16 (100 mg, 0.24 mmol), 1-cyclopropylmethyl-1H-indol-5-ylamine 19 (48 mg, 0.26 mmol), pyridinium hydrochloride (33 mg, 0.284 mmol), and phenol (155 mg, 1.652 mmol). The vial was capped and heated overnight at 110° C. The vial was cooled to room temperature and the residue taken up in CHCl3 and washed with 15% aqueous NaOH, water, brine, and dried (MgSO4). The solvent was removed and the residue purified by flash chromatography (silica gel, EtOAc:MeOH, 95:5) to provide compound 18 (88 mg, 0.159 mmol) as a light brown solid in 67% yield. For compound 18: MS (Cl) m/e 515 (M++1, 100); HPLC, rt=4.83 min.

Workup

  1. customThe vial was capped
  2. temperatureThe vial was cooled to room temperature
  3. washwashed with 15% aqueous NaOH, water, brine
  4. dry with materialdried (MgSO4)
  5. customThe solvent was removed
  6. customthe residue purified by flash chromatography (silica gel, EtOAc:MeOH, 95:5)

Sources & evidence

ORD record
ord-c127c03ba397458da51e66d86ca1f17e
Source dataset
uspto-grants-2005_03
Patent number
US06867201B2

Reaction notes

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