m-Aminoacetanilide → N-[3-[[3-Cyclopropyl-1-(2-fluoro-4-iodophenyl)-1,2,3,4,7,8-hexahydro-6,8-dimethyl-2,4,7-trioxopyrido[2,3-d]pyrimidin-5-yl]amino]phenyl]acetamide

HRID 75662

Reaction equation

[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11](OS(C4C=CC(C)=CC=4)(=O)=O)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:5]2=[O:37])[CH2:3][CH2:2]1.[NH2:38][C:39]1[CH:40]=[C:41]([CH:46]=[CH:47][CH:48]=1)[NH:42][C:43](=[O:45])[CH3:44].CN(C)C(=O)C.N1C(C)=CC=CC=1C>CO>[CH:1]1([N:4]2[C:9](=[O:10])[C:8]3[C:11]([NH:38][C:39]4[CH:40]=[C:41]([NH:42][C:43](=[O:45])[CH3:44])[CH:46]=[CH:47][CH:48]=4)=[C:12]([CH3:17])[C:13](=[O:16])[N:14]([CH3:15])[C:7]=3[N:6]([C:29]3[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=3[F:36])[C:5]2=[O:37])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

To p-toluenesulfonic acid 3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 77 (28.0 g) and 3′-aminoacetanilide 57 (13.2 g) were added N,N-dimethylacetamide (84.0 ml) and 2,6-lutidine (15.3 ml), and the mixture was stirred at 130° C. for 4 hrs. After allowing to cool with stirring, methanol (196 ml) was added dropwise, and the mixture was stirred at room temperature. The crystals were collected by filtration and dried to give N-{3-[3-cyclopropyl-1-(2-fluoro-4-iodo-phenyl)-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-ylamino]-phenyl}-acetamide 58 (25.2 g, yield 93%) as colorless crystals.

Workup

temperatureto cool
stirringwith stirring
stirringthe mixture was stirred at room temperature
filtrationThe crystals were collected by filtration
customdried

Sources & evidence

ORD record: ord-bb281ffcbca54202ac961e5332aaec1a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Linked notes

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