Methylamine → 3-Amino-N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-4,4,4-trifluorobutanamide

HRID 540173Notes

Reaction equation

[O:1]=[S:2]1(=[O:44])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5]([C:13]2[CH:22]=[C:21]([NH:23][C:24](=[O:42])[CH2:25][CH:26]([N:31]3C(=O)C4C(=CC=CC=4)C3=O)[C:27]([F:30])([F:29])[F:28])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH3:43])[CH:19]=3)[N:14]=2)[CH2:4][CH2:3]1.CN>C(O)C>[NH2:31][CH:26]([C:27]([F:28])([F:29])[F:30])[CH2:25][C:24]([NH:23][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH3:43])[CH:19]=2)[N:14]=[C:13]([N:5]2[CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[S:2](=[O:44])(=[O:1])[CH2:3][CH2:4]2)[CH:22]=1)=[O:42]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of N-[2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-6-methylquinolin-4-yl]-3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-4,4,4-trifluorobutanamide (25 mg, 0.04 mmol) in ethanol (3 mL) was added a solution of methylamine (30% in ethanol, 0.3 mL). The resulting mixture was heated at 90° C. for 2 hours. After being cooled to room temperature, the mixture was concentrated in vacuo. The residue was purified by flash chromatography (eluting with 50% ethyl acetate in hexanes) to afford 15 mg of the title compound as light solid (yield was 80%).

Workup

temperatureAfter being cooled to room temperature
concentrationthe mixture was concentrated in vacuo
customThe residue was purified by flash chromatography (eluting with 50% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-4bd7762df2064676a912bc7acc1545a4
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871756B2

Reaction notes

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