Diisopropylethylamine → HCID 71272465, compound

HRID 1771849Notes

Reaction equation

Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[NH:10][C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[CH:12][C:3]=12.[NH2:20][CH2:21][C:22]1[C:23]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])=[N:24][CH:25]=[CH:26][CH:27]=1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[C:8]([C:7]1[C:2]([NH:20][CH2:21][C:22]2[C:23]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])=[N:24][CH:25]=[CH:26][CH:27]=2)=[C:3]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[NH:10][C:4]2=[N:5][CH:6]=1)#[N:9]

Participants

Conditions

Temperature: 170 °C

Procedure

4-Chloro-2-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (30 mg, 0.11 mmol), N-(3-aminomethylpyridin-2-yl)-N-methylmethanesulfonamide (159 mg, 0.552 mmol) and N-ethyldiisopropylamine (0.282 ml, 1.656 mmol) are suspended in 0.4 ml of 1-methyl-2-pyrrolidone and heated in a microwave at 170° C. for 40 min. The reaction is still not complete even after a further 40 min, so that a further equivalent of N-(3-aminomethylpyridin-2-yl)-N-methylmethanesulfonamide (31.8 mg, 0.110 mmol) is added, and the batch is heated at 170° C. for a further 60 min. For work-up, the batch is partitioned between water and ethyl acetate, the organic phase is dried (Na2SO4) and evaporated, giving a brown oil, which is purified by chromatography; yield: 17 mg (34%); LC-MS: 451 [M+H]+; HPLC: 3.07 (RT/min).

Workup

additionis added
temperaturethe batch is heated at 170° C. for a further 60 min
customFor work-up, the batch is partitioned between water and ethyl acetate
dry with materialthe organic phase is dried (Na2SO4)
customevaporated
customgiving a brown oil, which
customis purified by chromatography
custom3.07 (RT/min)

Sources & evidence

ORD record: ord-e9fc8ba602f64eb8a8c288835fa9c91b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249140B2

Reaction notes

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