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Diisopropylethylamine → 2-[(6-{4-[2-(1,1-Dioxidothiomorpholin-4-yl)ethyl]piperazin-1-yl}pyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile

HRID 1241409
Notes
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Reaction equation

HRID 1241409 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[S:15][C:16]([C:19]#[N:20])=[CH:17][N:18]=3)[CH:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[Cl-].Cl[CH2:23][CH2:24][NH+:25]1[CH2:30][CH2:29][S:28](=[O:32])(=[O:31])[CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>CN(C=O)C>[O:31]=[S:28]1(=[O:32])[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:4]2[CH2:5][CH2:6][N:1]([C:7]3[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]4[S:15][C:16]([C:19]#[N:20])=[CH:17][N:18]=4)[CH:8]=3)[CH2:2][CH2:3]2)[CH2:26][CH2:27]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 219346302-(6-(Piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrileHCID 219346814-(2-Chloroethyl)thiomorpholin-4-ium 1,1-dioxide chloride

Product 1

HCID 210599652-[(6-{4-[2-(1,1-Dioxidothiomorpholin-4-yl)ethyl]piperazin-1-yl}pyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Conditions

Temperature
200 °C

Procedure

12-3 (0.20 g, 0.39 mmol), 41-2 (0.11 g, 0.47 mmol) and DIEA (0.30 g, 2.33 mmol) were suspended in DMF (1 mL) in a sealed tube and heated at 200° C. for 15 minutes in the Smith personal chemistry microwave reactor. The crude material was purified on a C18 preparative hplc column to afford 41-3. Hi-Res MS: calc: 449.1576 found: 449.1532. 1H-NMR(CD3OD): 8.49(s, 1H); 8.02(s, 1H); 6.28(s, 1H); 4.02(m, 4H); 3.48(br s, 4H); 3.39(t, 2H); 3.16(m, 4H); 3.12(m, 4H); 2.97(m, 2H).

Workup

  1. customThe crude material was purified on a C18 preparative hplc column
  2. customto afford 41-3

Sources & evidence

ORD record
ord-7a1b36a209a440f0adfd4ff5703ab013
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07115597B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes