Diisopropylethylamine → HCID 178428262, compound

HRID 452859Notes

Reaction equation

[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:15])[O:8][C@@H:9]([CH3:14])[C:10]([F:13])([F:12])[F:11])[CH2:2]1.Cl[C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:28]=[CH:27][NH:26][N:25]=2)[CH:20]=[C:19]([CH3:29])[N:18]=1.CCN(C(C)C)C(C)C>CS(C)=O>[F:12][C:10]([F:13])([F:11])[C@@H:9]([O:8][C:7](=[O:15])[NH:6][C@H:3]1[CH2:4][CH2:5][N:1]([C:17]2[N:18]=[C:19]([CH3:29])[CH:20]=[C:21]([NH:23][C:24]3[CH:28]=[CH:27][NH:26][N:25]=3)[N:22]=2)[CH2:2]1)[CH3:14]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of (2S)-1,1,1-trifluoropropan-2-yl (3S)-pyrrolidin-3-ylcarbamate (50 mg) in DMSO (5 ml) was added 2-chloro-6-methyl-N-(1H-pyrazol-3-yl)pyrimidin-4-amine (46 mg) prepared in Referential Example 1 and DIEA (28 mg) at room temperature. The resulting mixture was stirred at 110° C. for 15 hours and then cooled to room temperature. The mixture was purified with preparative RP-HPLC to give (2S)-1,1,1-trifluoropropan-2-yl{(3S)-1-[4-methyl-6-(1H-pyrazol-3-ylamino)pyrimidin-2-yl]pyrrolidin-3-yl}carbamate as a pale yellow solid.

Workup

temperaturecooled to room temperature
customThe mixture was purified with preparative RP-HPLC

Sources & evidence

ORD record: ord-3f3c49aad2ca45af99729bb2e5dd8126
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492397B2

Reaction notes

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