Diisopropylethylamine → HCID 57715131, compound

HRID 1984949Notes

Reaction equation

HRID 1984949 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:24]=[CH:23][C:7]([CH2:8][NH:9][C:10]2[N:19]=[C:18]([N:20]([CH3:22])[CH3:21])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=2)=[CH:6][CH:5]=1.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:28]([O:36][C:37]([F:40])([F:39])[F:38])[CH:27]=1.C(N(C(C)C)CC)(C)C>CC(O)C>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32]([NH:2][CH2:3][C:4]2[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:10]3[N:19]=[C:18]([N:20]([CH3:22])[CH3:21])[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]=3)=[CH:23][CH:24]=2)(=[O:34])=[O:33])=[C:28]([O:36][C:37]([F:39])([F:38])[F:40])[CH:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 68846786HCID 68846786, compound

Product 1

HCID 57715131HCID 57715131, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of N2-(4-aminomethyl-benzyl)-N4,N4-dimethyl-quinazoline-2,4-diamine hydrochloride (50.0 mg, 0.131 mmol), 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (53.3 mg, 0.157 mmol) and diisopropylethylamine (91 μl, 0.524 mmol) in 2-propanol (1.5 mL) was stirred at ambient temperature for 2 hr. The resulting mixture was concentrated, and the residue was purified by column chromatography (silica gel, 10% MeOH in CH2Cl2) to give 4-bromo-N-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-benzyl}-2-trifluoromethoxy-benzenesulfonamide as a white crystalline compound (40 mg, 50%).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel, 10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-dd5d8183c1b24abc97932a42d36a1e0c
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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