4-Methylmorpholine → (6S,7S)-N(7)-Hydroxy-5-methyl-N(6)-{4-[(2-methylquinolin-4-yl)methoxy]phenyl}-5-azaspiro[2.5]octane-6,7-dicarboxamide

HRID 1664616Notes

Reaction equation

HRID 1664616 reaction equation
F[P-](F)(F)(F)(F)F.[N:8]1([O:17][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH3:28][N:29]1[C@H:36]([C:37]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][C:48]3[C:57]4[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=4)[N:51]=[C:50]([CH3:58])[CH:49]=3)=[CH:42][CH:41]=2)=[O:38])[C@@H:35]([C:59](O)=[O:60])[CH2:34][C:31]2([CH2:33][CH2:32]2)[CH2:30]1.Cl.NO.CN1CCOCC1>CN(C=O)C>[OH:17][NH:8][C:59]([C@H:35]1[CH2:34][C:31]2([CH2:32][CH2:33]2)[CH2:30][N:29]([CH3:28])[C@@H:36]1[C:37]([NH:39][C:40]1[CH:41]=[CH:42][C:43]([O:46][CH2:47][C:48]2[C:57]3[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=3)[N:51]=[C:50]([CH3:58])[CH:49]=2)=[CH:44][CH:45]=1)=[O:38])=[O:60]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 443297Hydroxyamine hydrochlorideHCID 67006214(6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylic acid

Product 1

HCID 86595547(6S,7S)-N(7)-Hydroxy-5-methyl-N(6)-{4-[(2-methylquinolin-4-yl)methoxy]phenyl}-5-azaspiro[2.5]octane-6,7-dicarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To BOP (120.0 mg, 0.24 mmol) was added to a solution of (6S,7S)-5-methyl-6-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}amino)carbonyl]-5-azaspiro[2.5]octane-7-carboxylic acid (140 mg, 0.20 mmol) in DMF (1.0 mL) at 0° C. followed by hydroxylamine hydrochloride (28.0 mg, 0.40 mmol). 4-methylmorpholine (0.07 mL, 0.70 mmol) was then added to the above mixture at 0° C. and stirred at this temperature for 2 h. The product (70 mg) was purified by preparative HPLC. ESI (M+H)+ 475.4.

Workup

  1. customThe product (70 mg) was purified by preparative HPLC

Sources & evidence

ORD record
ord-ca79ffadd80d41cfb1caaf0f1f019dce
Source dataset
uspto-grants-2011_10
Patent number
US08039471B2

Reaction notes

Loading…