p-Toluenesulfonic acid → HCID 86610975, compound

HRID 2354247Notes

Reaction equation

HRID 2354247 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([OH:10])(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH:12]1([NH:15][C:16](=[O:44])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([N:24]3[C:33](=[O:34])[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:35][C@H:36]5[CH2:40][CH2:39][N:38]([CH:41]([CH3:43])[CH3:42])[CH2:37]5)[CH:31]=4)[N:26]=[CH:25]3)[CH:18]=2)[CH2:14][CH2:13]1>C(OCC)(=O)C>[C:1]1([CH3:11])[CH:2]=[CH:3][C:4]([S:7]([OH:10])(=[O:8])=[O:9])=[CH:5][CH:6]=1.[CH:12]1([NH:15][C:16](=[O:44])[C:17]2[CH:22]=[CH:21][C:20]([CH3:23])=[C:19]([N:24]3[C:33](=[O:34])[C:32]4[C:27](=[CH:28][CH:29]=[C:30]([O:35][C@H:36]5[CH2:40][CH2:39][N:38]([CH:41]([CH3:42])[CH3:43])[CH2:37]5)[CH:31]=4)[N:26]=[CH:25]3)[CH:18]=2)[CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11374246HCID 11374246, compound

Product 1

HCID 86610975HCID 86610975, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Using an analogous procedure to that described in Example 45, a 0.1N solution of 4-toluenesulfonic acid in ethyl acetate was reacted N-cyclopropyl-3-[6-{[(3S)-1-isopropylpyrrolidin-3-yl]oxy}-4-oxoquinazolin-3(4H)-yl]-4-methylbenzamide to gave the title compound; NMR Spectrum: (DMSOd6) 0.57 (m, 2H), 0.70 (m, 2H), 1.29 (m, 6H), 2.15 (s, 3H), 2.29 (m, 4H), 2.86 (m, 1H), 3.30 (m, 2H), 3.51 (m, 2H), 3.71 (m, 2H), 5.38 (m, 1H), 7.12 (d, 2H), 7.49 (d, 2H), 7.55 (m, 2H), 7.64 (d, 1H), 7.80 (d, 1H), 7.84 (m, 1H), 7.92 (m, 1H), 8.25 (s, 1H), 8.45 (d, 1H), 9.88 (d, 1H).

Sources & evidence

ORD record
ord-a6947e267b03480093a5e8bec09a3597
Source dataset
uspto-grants-2010_07
Patent number
US07750154B2

Reaction notes

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