Dimethylformamide → HCID 22048213, compound

HRID 1830848Notes

Reaction equation

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

Participants

Conditions

Temperature: 62.5 °C

Procedure

To a mixture of phthalimide potassium (6.2 kg) and dimethylformamide (110.74 L) was added 3-chloro-2-chloromethyl-5,8-dihydro-4-(4-methoxyphenyl)-6H-thiopyrano-[4′,3′:4,5]thieno[2,3-b]pyridine (11.055 kg) obtained in Reference Example 27 and the mixture was stirred at 60 to 65° C. for 1 hour. After cooling to 25° C., water (36.91 L) was added dropwise thereto and the mixture was stirred at the same temperature for 1 hour. The crystals deposited was filtered off and washed with water (29.14 L) to obtain the titled compound (14.057 kg, 99.4%). 1H-NMR (CDCl3) δ: 2.14 (2H, t, J=5.7 Hz), 2.64 (2H, t, J=5.7 Hz), 3.80 (2H, s), 3.89 (3H, s), 5.20 (2H, s), 6.98–7.13 (2H, s), 6.98–7.13 (3H, m), 7.75–7.78 (2H, m), 7.79–7.794 (2H, m).

Workup

customobtained in Reference Example 27
temperatureAfter cooling to 25° C.
stirringthe mixture was stirred at the same temperature for 1 hour
filtrationThe crystals deposited was filtered off
washwashed with water (29.14 L)

Sources & evidence

ORD record: ord-6f2771e6f33a450cac984722835fdb12
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07067527B2

Reaction notes

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