Diisopropylethylamine → 3-(4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperazin-1-yl)-N-methylpyrrolidine-1-carboxamide

HRID 1241420Notes

Reaction equation

HRID 1241420 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.[CH3:16][NH:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH2:21]1)=[O:19].CCN(C(C)C)C(C)C>C(O)CCC>[C:14]([C:11]1[S:10][C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([N:28]3[CH2:29][CH2:30][N:25]([CH:22]4[CH2:23][CH2:24][N:20]([C:18]([NH:17][CH3:16])=[O:19])[CH2:21]4)[CH2:26][CH2:27]3)[CH:3]=2)=[N:13][CH:12]=1)#[N:15]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 116873242-[(6-Chloropyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrileHCID 21934633N-methyl-3-piperazin-1-ylpyrrolidine-1-carboxamide

Product 1

HCID 219346793-(4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}piperazin-1-yl)-N-methylpyrrolidine-1-carboxamide

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

35-1 (0.106 g, 0.45 mmol), 45-5 (0.095 g, 0.45 mmol) and DIEA (0.18 g, 1.79 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 45-6. Hi-Res MS: calc: 414.1819 found: 414.1827. 1H-NMR (DMSO-d6): 12.08(s, 1H); 8.42(s, 1H); 8.26(s, 1H); 6.22(s, 1H); 6.02(d, 1H); 3.55(m, 4H); 3.38 (m, 1H); 3.13(m, 1H); 2.97(m, 1H); 2.78(m, 1H); 2.50(complex, 6H); 2.45(m, 2H); 2.06(m, 1H); 1.69(m, 1H).

Workup

  1. temperatureUpon cooling the precipitate
  2. filtrationwas filtered off
  3. washwashed with n-butanol and ethyl ether
  4. customdried
  5. customto afford 45-6

Sources & evidence

ORD record
ord-d924f1b7951440c18e0dfe5c5151be07
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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