N-methyl-2-pyrrolidone → HCID 57725590, compound

HRID 2370539Notes

Reaction equation

HRID 2370539 reaction equation
CS([C:4]1[S:5][C:6]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH:15]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1)=O.[C@@H:27]1(N)[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[NH2:33].CCN(C(C)C)C(C)C.CN1C(=[O:50])CCC1>>[OH:50][C@@H:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C@H:28]1[NH:33][C:4]1[S:5][C:6]2[CH:12]=[C:11]([O:13][C:14]3[CH:19]=[CH:18][N:17]=[C:16]([C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])[CH:15]=3)[CH:10]=[CH:9][C:7]=2[N:8]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 438061,2-Diaminocyclohexane, trans-HCID 81531DiisopropylethylamineHCID 57725687HCID 57725687, compound

Product 1

HCID 57725590HCID 57725590, compound

Conditions

Temperature
100 °C

Procedure

To the solution of tert-butyl 4-(2-(methylsulfinyl)benzo[d]thiazol-6-yloxy)picolinate (500 mg, 1.25 mmol) in 10 ml of NMP was added (1R,2R)-cyclohexane-1,2-diamine (581 mg, 3.84 mmol) and DIPEA (0.995 ml, 5.76 mmol). The reaction solution was stirred at 100° C. for 3 days. The crude reaction solution was purified on prep HPLC and evaporated in vaccuo to give tert-butyl 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinate (240 mg, 0.544 mmol) as white powder. ES/MS m/z 442.5 (MH+).

Workup

  1. customThe crude reaction solution
  2. customwas purified on prep HPLC
  3. customevaporated in vaccuo

Sources & evidence

ORD record
ord-84b80b53bb1d474b99c6aee86d9c27ca
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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