p-Toluenesulfonic acid → HCID 86640911, compound

HRID 239000Notes

Reaction equation

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:17][CH2:18][CH2:19][O:20][CH3:21])=[C:9]([O:12][CH2:13][CH2:14][O:15][CH3:16])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:22][C:23]1[CH:24]=[C:25]([C:29]#[CH:30])[CH:26]=[CH:27][CH:28]=1.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(OCC)(=O)C>[CH3:16][O:15][CH2:14][CH2:13][O:12][C:9]1[CH:10]=[C:11]2[C:2]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[CH:30])[CH:24]=3)=[N:3][CH:4]=[N:5][C:6]2=[CH:7][C:8]=1[O:17][CH2:18][CH2:19][O:20][CH3:21].[S:37]([C:34]1[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=1)([O-:40])(=[O:39])=[O:38]

Participants

Conditions

Temperature: 37.5 °C

Procedure

5.0 g of 4-chloro-6,7-bis (2-methoxyethoxy) quinazoline was suspended in 75 ml ethyl acetate and 2.55 g of 3-aminophenyl acetylene was charged at 25-30° C. 0.9 g of p-toluyl sulphonic acid was added. The reaction mass was heated and stirred at 35-40° C. for 2 hours. The solid obtained was filtered and washed with ethyl acetate. The product was dried at 38-40° C. to obtain 6.6 g of erlotinib tosylate.

Workup

temperatureThe reaction mass was heated
customThe solid obtained
filtrationwas filtered
washwashed with ethyl acetate
customThe product was dried at 38-40° C.

Sources & evidence

ORD record: ord-d6ebd005b0a443bca6c51150bc84be22
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642758B2

Reaction notes

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