Methanol → HCID 54583358, compound

HRID 1914769Notes

Reaction equation

HRID 1914769 reaction equation
C([O:8][CH2:9][C@@H:10]1[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][N:11]1[C:17]1[CH:18]=[CH:19][C:20]([O:41][C:42]([F:45])([F:44])[F:43])=[C:21]([NH:23][C:24]2[N:33]=[CH:32][C:31]3[CH2:30][CH2:29][C:28]4[C:34]([C:38]([NH2:40])=[O:39])=[N:35][N:36]([CH3:37])[C:27]=4[C:26]=3[N:25]=2)[CH:22]=1)C1C=CC=CC=1.B(Cl)(Cl)Cl.CO>C(Cl)Cl>[OH:8][CH2:9][C@@H:10]1[CH2:15][N:14]([CH3:16])[CH2:13][CH2:12][N:11]1[C:17]1[CH:18]=[CH:19][C:20]([O:41][C:42]([F:43])([F:44])[F:45])=[C:21]([NH:23][C:24]2[N:33]=[CH:32][C:31]3[CH2:30][CH2:29][C:28]4[C:34]([C:38]([NH2:40])=[O:39])=[N:35][N:36]([CH3:37])[C:27]=4[C:26]=3[N:25]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 68668848HCID 68668848, compound

Product 1

HCID 54583358HCID 54583358, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 8-[5-((S)-2-benzyloxymethyl-4-methyl-piperazin-1-yl)-2-trifluoromethoxy-phenylamino]-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide (53 mg, 0.08 mmol) in DCM (1.7 mL) under an atmosphere of N2, at −78° C. 1M BCl3 in DCM (0.17 mL) was added dropwise. Under complete addition the solution was stirred at 0° C. for 30 min and at room temperature overnight. Then 2 mL of MeOH was added. The solvent was removed under reduced pressure and the residue was diluted with Et2O and decanted to give the desired compound in quantitative yield (46 mg) as a brown solid.

Workup

  1. customat −78° C
  2. additionUnder complete addition the solution
  3. customThe solvent was removed under reduced pressure
  4. additionthe residue was diluted with Et2O
  5. customdecanted

Sources & evidence

ORD record
ord-40282f6a925d4fc699ba8e11c5ca839f
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

Loading…