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

HRID 1241416Notes

Reaction equation

HRID 1241416 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[S:10][C:11]([C:14]#[N:15])=[CH:12][N:13]=2)[CH:3]=1.[N:16]1([CH2:22][CH2:23][N:24]2[CH2:28][CH2:27][NH:26][C:25]2=[O:29])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.CCN(C(C)C)C(C)C>C(O)CCC>[O:29]=[C:25]1[NH:26][CH2:27][CH2:28][N:24]1[CH2:23][CH2:22][N:16]1[CH2:21][CH2:20][N:19]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[S:10][C:11]([C:14]#[N:15])=[CH:12][N:13]=3)[CH:3]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrileHCID 142083331-[2-(Piperazin-1-yl)ethyl]imidazolidin-2-one

Product 1

HCID 219346292-[(6-{4-[2-(2-Oxoimidazolidin-1-yl)ethyl]piperazin-1-yl}pyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

35-1 (0.25 g, 1.06 mmol), 44-4 (0.21 g, 1.06 mmol) and DIEA (0.69 g, 5.32 mmol) were heated at 150° C. for 3 hours in n-butanol. Upon cooling the precipitate was filtered off, washed with n-butanol and ethyl ether and then dried to afford 44-5. Hi-Res MS: calc: 400.1663 found: 400.1633. 1H-NMR (CD3OD): 8.38(s, 1H); 7.99(s, 1H); 6.14(s, 1H); 3.65(m, 4H); 3.55(m, 2H); 3.39(m, 2H); 3.35(t, 2H); 2.59(complex, 6H).

Workup

  1. temperatureUpon cooling the precipitate
  2. filtrationwas filtered off
  3. washwashed with n-butanol and ethyl ether
  4. customdried
  5. customto afford 44-5

Sources & evidence

ORD record
ord-13d2b9d1df6644fbb64a0410e6dfb933
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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