Cyclopropylamine → HCID 57725524, compound

HRID 1988451Notes

Reaction equation

HRID 1988451 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH:8][C:9]1[S:10][C:11]2[CH:17]=[C:16]([O:18][C:19]3[CH:24]=[CH:23][N:22]=[C:21]([C:25](O)=[O:26])[CH:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1.CN(C(ON1N=NC2[CH:39]=[CH:40][CH:41]=[N:42]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>CN1C(=O)CCC1>[CH:41]1([NH:42][C:25](=[O:26])[C:21]2[CH:20]=[C:19]([O:18][C:16]3[CH:15]=[CH:14][C:12]4[N:13]=[C:9]([NH:8][C@@H:3]5[CH2:4][CH2:5][CH2:6][CH2:7][C@H:2]5[OH:1])[S:10][C:11]=4[CH:17]=3)[CH:24]=[CH:23][N:22]=2)[CH2:39][CH2:40]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57725526HCID 57725526, compound

Product 1

HCID 57725524HCID 57725524, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To the reaction solution of 4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinic acid (5 mg, 39 μmol), HATU (15 mg, 39 μmol) and DIPEA (14 μL, 78 μmol) in 1 ml of NMP was added cyclopropylamine (7 ul mg, 30 μmol). The reaction solution was stirred at room temperature for 12 hours. The crude reaction solution was purified on prep HPLC and evaporated in vacuo to give N-cyclopropyl-4-(2-((1R,2R)-2-hydroxycyclohexylamino)benzo[d]thiazol-6-yloxy)picolinamide (1 mg, 2.3 μmol) as white powder. ES/MS m/z 425.2 (MH+).

Workup

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

Sources & evidence

ORD record
ord-f59cc971b05147e5bca99824e3443dfd
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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