Diisopropylethylamine → HCID 59518957, compound

HRID 1161875Notes

Reaction equation

HRID 1161875 reaction equation
[N:1]1([C:8]2[CH:9]=[C:10]3[C:15](=[CH:16][CH:17]=2)[N:14]=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([O:25][CH3:26])[CH:19]=2)[N:12]([CH2:27][C:28]([NH:30][CH:31]([CH3:33])[CH3:32])=[O:29])[C:11]3=[O:34])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CC1C=CC(S(O[CH2:46][CH:47]2[CH2:52][CH2:51][O:50][CH2:49][CH2:48]2)(=O)=O)=CC=1.CCN(C(C)C)C(C)C>CN(C=O)C>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[N:12]([CH2:27][C:28]([NH:30][CH:31]([CH3:32])[CH3:33])=[O:29])[C:11](=[O:34])[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([N:1]4[CH2:7][CH2:6][CH2:5][N:4]([CH2:46][CH:47]5[CH2:52][CH2:51][O:50][CH2:49][CH2:48]5)[CH2:3][CH2:2]4)[CH:9]=3)[N:14]=2)=[CH:19][C:20]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 19077576(Tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonateHCID 59519086HCID 59519086, compound

Product 1

HCID 59518957HCID 59518957, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(6-(1,4-Diazepan-1-yl)-2-(4-fluoro-3-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl)-N-isopropylacetamide (EXAMPLE 1i) (30 mg, 0.064 mmol), (tetrahydro-2H-pyran-4-yl)methyl 4-methylbenzenesulfonate (35 mg, 0.128 mmol) and DIPEA (17 mg, 21 μl, 0.128 mmol) were dissolved in DMF (1 mL) and stirred at room temperature overnight. Purification by preparative HPLC afforded 2-{2-(4-fluoro-3-methoxyphenyl)-4-oxo-6-[4-(tetrahydropyran-4-ylmethyl)perhydro-1,4-diazepin-1-yl]-4H-quinazolin-3-yl}-N-isopropylacetamide (EXAMPLE 11a) (5 mg, 0.0088 mmol, 14%).

Workup

  1. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-d397a053a3224b99b8025c83bca56466
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

Loading…