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

HRID 1241425Notes

Reaction equation

HRID 1241425 reaction equation
[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([N:15]3[CH2:20][CH2:19][N:18](C(OCC4C=CC=CC=4)=O)[CH:17]([C:31]([NH:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:16]3)[CH:10]=2)=[N:5][CH:4]=1)#[N:2].C1(OC)C=CC=CC=1>F>[C:1]([C:3]1[S:7][C:6]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([N:15]3[CH2:20][CH2:19][NH:18][CH:17]([C:31]([NH:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:16]3)[CH:10]=2)=[N:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 21934713Benzyl 4-{6-[(5-cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-2-[(isopropylamino) carbonyl]piperazine-1-carboxylate

Product 1

HCID 219346924-{6-[(5-Cyano-1,3-thiazol-2-yl)amino]pyrimidin-4-yl}-N-isopropylpiperazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 14917Hydrofluoric AcidSolvent

Procedure

47-3 (0.23 g, 0.46 mmol) was wetted with 1 mL of anisole before treatment with 10 mL of hydrofluoric acid for 1 hour at 0° C. The hydrofluoric acid was then evaporated off and the residue was suspended in ethyl ether, filtered and then purified on a silica column to give 48-1. Hi-Res MS: calc: 373.1554 found: 373.1550. 1H-NMR (CD3OD): 8.40(s, 1H); 7.99(s, 1H); 6.17(s, 1H); 4.30(d, 1H); 3.98(m, 2H); 3.37(m, 1H); 3.18(m, 2H); 3.06(m, 1H); 2.82(m, 1H); 1.16(m, 6H).

Workup

  1. customThe hydrofluoric acid was then evaporated off
  2. filtrationfiltered
  3. custompurified on a silica column
  4. customto give 48-1

Sources & evidence

ORD record
ord-f432f5b47f7641fa81d37fe6b48dccef
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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