Diisopropylethylamine → 2S9KS24Syb

HRID 1771932Notes

Reaction equation

Cl[C:2]1[N:3]=[C:4]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[C:5]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][S:8][C:6]=2[N:7]=1.[OH:25][CH2:26][CH2:27][NH:28][C:29]([CH:31]1[CH2:36][CH2:35][CH2:34][NH:33][CH2:32]1)=[O:30].C(N(CC)C(C)C)(C)C>CN1C(=O)CCC1>[OH:25][CH2:26][CH2:27][NH:28][C:29]([CH:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:2]2[N:3]=[C:4]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[C:5]3[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=4)=[CH:9][S:8][C:6]=3[N:7]=2)[CH2:32]1)=[O:30]

Participants

Conditions

Temperature: 200 °C

Procedure

(2-Chloro-5-phenyl-thieno[2,3-d]pyrimidin-4-yl)-pyridin-2-ylmethyl-amine (44 mg, 0.124 mmol), Piperidine-3-carboxylic acid(2-hydroxyethyl)amide (Fluorochem, 32 mg, 0.188 mmol, 1.5 eq) and N,N-diisopropylethylamine (Aldrich, 0.188 mmol) were dissolved in N-Methyl Pyrrolidinone (1.5 ml) in a Biotage microwave tube and heated to 200° C. and maintained at this temperature for 30 min. On cooling, the solvents were removed in vacuo. The residue was triturated with DCM (2×10 ml) and the extracts combined, concentrated and purified by prep TLC (eluent 10% MeOH/DCM) to give the product as a yellow oil, which slowly solidified on standing to a waxy solid. The waxy solid may be converted to a free-flowing powder by stirring in diethyl ether for 1-2 h (0.5 g in 10 ml). Yield=18.3 mg (30%)

Workup

temperaturemaintained at this temperature for 30 min
temperatureOn cooling
customthe solvents were removed in vacuo
customThe residue was triturated with DCM (2×10 ml)
concentrationconcentrated
custompurified by prep TLC (eluent 10% MeOH/DCM)

Sources & evidence

ORD record: ord-abf35a90979c4b8fa90423c138ee78ae
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249155B2

Reaction notes

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