Pyrrolidine → HCID 86720283, compound

HRID 1777486Notes

Reaction equation

HRID 1777486 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH:9][C:10]2[S:11][C:12]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=4)[CH:16]=[CH:15][C:13]=3[N:14]=2)[CH:4]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>O1CCOCC1>[N:22]1[CH:23]=[CH:24][C:19]([C:17]2[CH:16]=[CH:15][C:13]3[N:14]=[C:10]([NH:9][C:5]4[CH:4]=[C:3]([CH2:2][N:25]5[CH2:29][CH2:28][CH2:27][CH2:26]5)[CH:8]=[CH:7][N:6]=4)[S:11][C:12]=3[CH:18]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 81531DiisopropylethylamineHCID 86720282HCID 86720282, compound

Product 1

HCID 86720283HCID 86720283, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A solution of N-(4-(chloromethyl)pyridin-2-yl)-6-(pyridin-4-yl)benzo[d]thiazol-2-amine (80 mg, 0.23 mmol, 1 eq.) in 1 mL dioxane was treated with 15 mg of pyrrolidine and 20 mg DIEA. The reaction mixture was stirred at 140° C. under microwave condition for 1 h. After cooling to rt, the mixture was concentrated in vacuo. The residue was washed with EtOH to afford 6-(pyridin-4-yl)-N-(4-(pyrrolidin-1-ylmethyl)pyridin-2-yl)benzo[d]thiazol-2-amine 102 without further purification (67 mg). 1HNMR (CD3OD, 400 MHz) δ 8.83 (d, 2H), 8.60 (m, 1H), 8.54 (m, 1H), 8.46 (m, 2H), 8.10 (m, 1H), 7.92 (d, 1H), 7.52 (s, 1H), 3.37 (d, 1H), 4.53 (s, 2H), 3.62 (br s, 2H), 3.25 (m, 2H overlapping with signal from CD3OD), 2.22 (m, 2H), 2.09 (m, 2H). MS (ES-API): MH+=388.1. HPLC tR=2.16 min.

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated in vacuo
  3. washThe residue was washed with EtOH

Sources & evidence

ORD record
ord-f31976ac205946429fae60bedfb7d552
Source dataset
uspto-grants-2016_02
Patent number
US09266874B2

Reaction notes

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