Trifluoroacetic acid → 2-({6-[4-(1,1-Dioxidothietan-3-yl)piperazin-1-yl]pyrimidin-4-yl}amino)-1,3-thiazole-5-carbonitrile

HRID 1241428Notes

Reaction equation

[O:1]=[S:2]1(=[O:19])[CH2:5][CH:4]([N:6]2[CH2:11][CH2:10][N:9]([C:12](OC(C)(C)C)=O)[CH2:8][CH2:7]2)[CH2:3]1.FC(F)(F)C(O)=O.ClC1[N:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]2[S:36][C:37]([C:40]#[N:41])=[CH:38][N:39]=2)[CH:29]=1.C(N(CC)CC)C>C(O)CCC>[O:19]=[S:2]1(=[O:1])[CH2:3][CH:4]([N:6]2[CH2:7][CH2:8][N:9]([C:12]3[N:33]=[CH:32][N:31]=[C:30]([NH:34][C:35]4[S:36][C:37]([C:40]#[N:41])=[CH:38][N:39]=4)[CH:29]=3)[CH2:10][CH2:11]2)[CH2:5]1

Participants

Conditions

Temperature: 150 °C

Procedure

50-2 (0.20 g, 0.68 mmol) was first treated with trifluoroacetic acid (4 mL) for 30 minutes and then concentrated under reduced pressure. The residue was then dissolved in n-butanol (4 mL) to which 35-1 (0.16 g, 0.68 mmol) and triethylamine (0.34 g, 3.41 mmol) were added and then heated at 150° C. for 18 hours. Upon cooling the solid was filtered off, washed with n-butanol, ethyl ether and then purified on a silica column to yield 50-3. Hi-Res MS: calc: 392.0958 found: 392.0949. 1H-NMR (DMSO-d6): 12.10(s, 1H); 8.43(s, 1H); 8.26(s, 1H); 6.24(s, 1H); 4.28(m, 2H); 4.15(m, 2H); 3.57(br s, 4H); 3.22(m, 1H); 2.46(t, 4H).

Workup

concentrationconcentrated under reduced pressure
additionwere added
temperatureUpon cooling the solid
filtrationwas filtered off
washwashed with n-butanol, ethyl ether
custompurified on a silica column
customto yield 50-3

Sources & evidence

ORD record: ord-f394c70de9d24461abf07effea333589
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115597B2

Reaction notes

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