Diisopropylethylamine → HCID 136368404, compound

HRID 2100560Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[NH:4][C:5](=[O:13])[C:6]2[CH:12]=[CH:11][CH:10]=[N:9][C:7]=2[N:8]=1.CCN(C(C)C)C(C)C.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][S:32](Cl)(=[O:34])=[O:33]>C(Cl)Cl>[O:13]=[C:5]1[NH:4][C:3]([CH2:2][NH:1][S:32]([CH2:31][CH2:30][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[F:23])(=[O:33])=[O:34])=[N:8][C:7]2[N:9]=[CH:10][CH:11]=[CH:12][C:6]1=2

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cooled suspension of 2-aminomethyl-3H-pyrido[2,3-d]pyrimidin-4-one (example 84.3; 50 mg, 0.28 mmol) in CH2Cl2 (2 ml) were added DIPEA (0.10 ml, 0.58 mmol) and 2-(2-fluoro-phenyl)-ethanesulfonyl chloride (78 mg, 0.35 mmol). The reaction mixture was stirred for 3 hours at 0° C. Unreacted 2-aminomethyl-3H-pyrido[2,3-d]pyrimidin-4-one was filtered off, the filtrate was evaporated to dryness and chromatographed (silica gel, EtOAc) to yield 2-(2-fluoro-phenyl)-ethanesulfonic acid (4-oxo-3,4-dihydro-pyrido[2,3-d]pyrimidin-2-ylmethyl)-amide (12 mg, 0.034 mmol; 12%) as a white solid. MS (m/e): 363.1 [M+H+].

Workup

filtrationwas filtered off
customthe filtrate was evaporated to dryness
customchromatographed (silica gel, EtOAc)

Sources & evidence

ORD record: ord-df3311c581a24c5f80f5781fde66000f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572801B2

Reaction notes

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