2486-69-3 → HCID 25255104, compound

HRID 1880908Notes

Reaction equation

Cl[C:2]1[N:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([F:15])([F:14])[CH2:8][N:7]([CH:16]3[CH2:20][CH2:19][C@@H:18]([CH3:21])[CH2:17]3)[C:6]=2[N:22]=1.[NH2:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=1[O:33][CH3:34].O.CC1C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[F:14][C:9]1([F:15])[CH2:8][N:7]([CH:16]2[CH2:20][CH2:19][C@@H:18]([CH3:21])[CH2:17]2)[C:6]2[N:22]=[C:2]([NH:23][C:24]3[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=3[O:33][CH3:34])[N:3]=[CH:4][C:5]=2[N:11]([CH3:12])[C:10]1=[O:13]

Participants

Conditions

Temperature: 85 °C

Procedure

2-Chloro-7,7-difluoro-5-methyl-9-((3R)-3-methylcyclopentyl)-8,9-dihydro-5H-pyrimido[4,5-b][1,4]diazepin-6(7H)-one (500 mg, 1.51 mmol) and 4-amino-3-methoxybenzoic acid (316.0 mg, 1.89 mmol) were weighed into a flask. 4-Methylbenzenesulfonic acid monohydrate (230.0 mg, 1.21 mmol) was weighed into a separate flask and dissolved in dioxane (15 ml). The toxic acid solution was then added to the flask containing the two starting materials. The reaction was stirred at 85° C. for 48 hours followed by 100° C. for an additional 48 hours. The dark brown mixture was cooled to room temperature and filtered through paper. The solids were washed with ethyl acetate (15 ml). m/z 462.4 (M+H)+.

Workup

additionThe toxic acid solution was then added to the flask
additioncontaining the two starting materials
waitfollowed by 100° C. for an additional 48 hours
temperatureThe dark brown mixture was cooled to room temperature
filtrationfiltered through paper
washThe solids were washed with ethyl acetate (15 ml)

Sources & evidence

ORD record: ord-880b7e4c845149dbac1accb8ffedbf89
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318727B2

Reaction notes

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