Morpholine → HCID 56953216, compound

HRID 712285Notes

Reaction equation

HRID 712285 reaction equation
B([C:4]1[C:12]2[S:11][C:10]([NH:13][C:14](=[O:18])[NH:15][CH2:16][CH3:17])=[N:9][C:8]=2[CH:7]=[C:6]([C:19]2[CH:20]=[N:21][C:22]([N:25]3[CH2:30][CH2:29][C:28]([CH2:34][CH3:35])([C:31]([OH:33])=[O:32])[CH2:27][CH2:26]3)=[N:23][CH:24]=2)[CH:5]=1)(O)O.C(N(CC)CC)C.[NH:43]1[CH2:48][CH2:47][O:46][CH2:45][CH2:44]1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:34]([C:28]1([C:31]([OH:33])=[O:32])[CH2:29][CH2:30][N:25]([C:22]2[N:21]=[CH:20][C:19]([C:6]3[CH:5]=[C:4]([N:43]4[CH2:48][CH2:47][O:46][CH2:45][CH2:44]4)[C:12]4[S:11][C:10]([NH:13][C:14](=[O:18])[NH:15][CH2:16][CH3:17])=[N:9][C:8]=4[CH:7]=3)=[CH:24][N:23]=2)[CH2:26][CH2:27]1)[CH3:35]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 86663998HCID 86663998, compound

Product 1

HCID 56953216HCID 56953216, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8895Cupric acetateSolvent

Procedure

1-[5-[7-borono-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-ethyl-piperidine-4-carboxylic acid (100 mg) was placed in DCM 5 ml and copper acetate 47 mg, triethylamine 122 mg, 4A molecular sieves (powdered) and morpholine 17 mg were added and the mixture stirred at rt over the weekend. LCMS showed that some desired product had formed and a close running 7-H impurity. The mixture was filtered and the solvent removed in vacuo to give a dark gum which was purified by preparative HPLC using a phenyl hexyl column eluting with 65-75% ACN to give Compound 114 as an off white solid (8 mg). 1H NMR (CDCl3) δ 8.52 (s, 2H), 7.38 (s, 1H), 6.84 (s, 1H), 4.50-4.42 (m, 2H), 3.89-3.85 (m, 4H), 3.35-3.29 (m, 4H), 3.21-3.17 (m, 4H), 2.22-2.14 (m, 2H), 1.61-1.54 (m, 2H), 1.45-1.35 (m, 2H), 1.19 (t, J=7.2 Hz, 3H), 0.86 (t, J=7.5 Hz, 3H). MS: 540.13 [M+H]+.

Sources & evidence

ORD record
ord-5c2ba495ee9848eca91d2a2b0dccf3c6
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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