Diisopropylethylamine → HCID 59420772, compound

HRID 499096Notes

Reaction equation

P(OCC)(OCC)([O:3][C:4]1([CH:8]2[CH2:10][CH2:9]2)[CH2:7][NH:6][CH2:5]1)=O.[CH3:17][C:18]1[NH:22][N:21]=[C:20]([NH:23][C:24]2[CH:29]=[C:28](Cl)[N:27]=[C:26]([S:31][C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39]([CH:41]4[CH2:43][CH2:42]4)=[O:40])=[CH:34][CH:33]=3)[N:25]=2)[CH:19]=1.[CH3:44]CN(C(C)C)C(C)C>CO>[CH3:17][C:18]1[NH:22][N:21]=[C:20]([NH:23][C:24]2[CH:29]=[C:28]([N:6]3[CH2:5][C:4]([CH:8]4[CH2:9][CH2:10]4)([O:3][CH3:44])[CH2:7]3)[N:27]=[C:26]([S:31][C:32]3[CH:37]=[CH:36][C:35]([NH:38][C:39]([CH:41]4[CH2:43][CH2:42]4)=[O:40])=[CH:34][CH:33]=3)[N:25]=2)[CH:19]=1

Participants

Conditions

Temperature: 65 °C

Procedure

3-Cyclopropylazetidin-3-yl diethyl phosphate (103 mg, 0.36 mmol) was added to a solution of N-(4-(4-(5-methyl-1H-pyrazol-3-ylamino)-6-chloropyrimidin-2-ylthio)phenyl)cyclopropanecarboxamide (96 mg, 0.24 mmol) and DIPEA (0.40 ml, 2.32 mmol) in methanol (5 ml), and the mixture was heated to 65° C. for 16 hours. The volatile components of the mixture were then removed in vacuo and the residue purified mass directed preparative HPLC, eluted with Acetonitrile/water/TFA to give the product as a white solid after freeze drying (6.3 mg, 5.3%). DMSO-d6: 0.34 (2H, m), 0.55 (2H, m), 0.81 (4H, d), 1.14 (1H, m), 1.81 (1H, m), 1.99 (3H, s), 3.26 (3H, s), 3.79 (4H, m), 5.37 (1H, s), 5.71 (1H, br s), 7.49 (2H, d), 7.71 (2H, d), 9.34 (1H, s), 10.39 (1H, s). ES+ 492

Workup

customThe volatile components of the mixture were then removed in vacuo
customthe residue purified mass
washeluted with Acetonitrile/water/TFA

Sources & evidence

ORD record: ord-49a9353e33da452ca94e96957eceb546
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767672B2

Reaction notes

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