Dimethyl Sulfoxide → HCID 131727715, compound

HRID 1432154Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

With warming to about 75° C., 4-(3′-chloro-4′-fluoroanilino)-7-methoxy-6-(3-morpholinopropoxy)quinazoline (204 kg) was dissolved in a mixture of ethyl acetate (1021 liters) and dimethyl sulphoxide (181 liters) containing diatomaceous earth filter aid (5 kg). The resultant mixture was filtered and ethyl acetate (78 liters) was used to wash the filter aid solid. The filtrate and washings were combined and cooled initially to about 10° C. The mixture was then heated to about 40° C. for 1 hour. The warm mixture was cooled to 0° C. at a rate of about 10° C. per hour. The resultant solid was collected by filtration. There was thus obtained Form 3 ZD1839 DMSO solvate as shown by XRPD and DSC analysis.

Workup

additioncontaining diatomaceous earth
filtrationfilter aid (5 kg)
filtrationThe resultant mixture was filtered
washto wash the filter aid solid
temperaturecooled initially to about 10° C
temperatureThe mixture was then heated to about 40° C. for 1 hour
temperatureThe warm mixture was cooled to 0° C. at a rate of about 10° C. per hour
filtrationThe resultant solid was collected by filtration

Sources & evidence

ORD record: ord-29301d8c00c240a0985908ab3ea9279a
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612077B2

Reaction notes

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