Methyl Isocyanate → 4-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-N-methylpiperazine-1-carboxamide

HRID 1241414Notes

Reaction equation

HRID 1241414 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.CCN(C(C)C)C(C)C.[CH3:30][N:31]=[C:32]=[O:33]>CN(C=O)C.C(Cl)Cl>[C:19]([C:16]1[S:15][C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([N:1]3[CH2:6][CH2:5][N:4]([C:32]([NH:31][CH3:30])=[O:33])[CH2:3][CH2:2]3)[CH:8]=2)=[N:18][CH:17]=1)#[N:20]

Participants

6

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 219346302-(6-(Piperazin-1-yl)pyrimidin-4-ylamino)thiazole-5-carbonitrile

Product 1

HCID 219346634-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-N-methylpiperazine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

12-3 (0.25 g, 0.88 mmol) was dissolved in a minimal amount of DMF (2 mL) and DIEA (0.57 g, 4.38 mmol) before it was diluted with methylene chloride (5 mL). Then a methylene chloride solution (1 mL) of methylisocyanate (0.050 g, 0.88 mmol) was added. A precipitate quickly formed and was filtered off, washed with methylene chloride and air dried to afford 43-1. Hi-Res MS: calc: 345.1241 found: 345.1269. 1H-NMR (DMSO-d6): 12.09(s, 1H); 8.44(s, 1H); 8.26(s, 1H); 6.52(d, 1H); 6.21(s, 1H); 3.54(m, 4H); 3.40(m, 4H); 2.58(d, 3H).

Workup

  1. customA precipitate quickly formed
  2. filtrationwas filtered off
  3. washwashed with methylene chloride and air
  4. customdried
  5. customto afford 43-1

Sources & evidence

ORD record
ord-1d57c68ad0a84b518dafef97bdd84d7a
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…