Triethylamine → HCID 58255013, compound

HRID 536403Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]([CH3:14])=[CH:4][C:3]=1[NH:15][C:16]1[N:21]=[C:20]([NH:22][C:23]2[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=2)[C:19]([C:29]([F:32])([F:31])[F:30])=[CH:18][N:17]=1.Br[CH2:34][CH:35]1[CH2:37][C:36]1([F:39])[F:38].C(N(CC)CC)C>CN(C=O)C>[F:38][C:36]1([F:39])[CH2:37][CH:35]1[CH2:34][N:11]1[CH2:10][CH2:9][CH:8]([C:6]2[C:5]([CH3:14])=[CH:4][C:3]([NH:15][C:16]3[N:21]=[C:20]([NH:22][C:23]4[CH:27]=[C:26]([CH3:28])[NH:25][N:24]=4)[C:19]([C:29]([F:32])([F:30])[F:31])=[CH:18][N:17]=3)=[C:2]([F:1])[CH:7]=2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N2-(2-fluoro-5-methyl-4-(piperidin-4-yl)phenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine (100 mg, 0.22 mmol), 2-(bromomethyl)-1,1-difluorocyclopropane (76.4 mg, 0.45 mmol) and triethylamine (60.6 μL, 0.42 mmol) in 1 mL of DMF was heated at 60° C. in a microwave reactor for 2 h. The crude product was purified by RP-HPLC to afford N2-(4-(1-((2,2-difluorocyclopropyl)methyl)piperidin-4-yl)-2-fluoro-5-methylphenyl)-N4-(5-methyl-1H-pyrazol-3-yl)-5-(trifluoromethyl)pyrimidine-2,4-diamine; ESMS m/z 540.2 (M+H+).

Workup

customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-8e737eebd30545629b56620e8d5db8a8
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859574B2

Reaction notes

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