4-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholine → 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(5-(morpholino-methyl)thiophen-2-yl)phenyl)propan-2-yl)acetamide

HRID 525596Notes

Reaction equation

HRID 525596 reaction equation
[Cl:1][CH:2]([Cl:18])[C:3]([NH:5][C@H:6]([CH2:16][F:17])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11](I)=[CH:10][CH:9]=1)=[O:4].CC1(C)C(C)(C)OB([C:27]2[S:31][C:30]([CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[CH:29][CH:28]=2)O1>>[Cl:1][CH:2]([Cl:18])[C:3]([NH:5][C@H:6]([CH2:16][F:17])[C@H:7]([OH:15])[C:8]1[CH:13]=[CH:12][C:11]([C:27]2[S:31][C:30]([CH2:32][N:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:29][CH:28]=2)=[CH:10][CH:9]=1)=[O:4]

Participants

3

Reactant 2

HCID 467390464-((5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholineHCID 683504732,2-dichloro-N-[(1S,2R)-1-(fluoromethyl)-2-hydroxy-2-(4-iodophenyl)ethyl]acetamide

Product 1

HCID 866954822,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-(5-(morpholino-methyl)thiophen-2-yl)phenyl)propan-2-yl)acetamide

Procedure

Following the general procedure of Example 22, Step 1 and making non-critical variations but using 2,2-dichloro-N-((1R,2S)-3-fluoro-1-hydroxy-1-(4-iodophenyl)propan-2-yl)acetamide (150 mg, 0.34 mmol) and 4-((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophen-2-yl)methyl)morpholine (114 mg, 0.37 mmol), followed by the general procedure from Example 2, step 2, the title compound is obtained (50 mg): 1H NMR (400 MHz, CDCl3) δ: 1.66 (bs, 1H), 2.53 (t, 4H), 3.71 (s, 2H,), 3.75 (t, 4H), 4.25-4.38 (m, 1H), 4.42-4.48 (m, 0.5H), 4.53-4.60 (m, 1H), 4.65-4.71 (m, 0.5H), 5.11 (d, 1H), 5.87 (s, 1H), 6.89 (d, J=3.5 Hz, 1H), 7.04 (d, J=8.8 Hz, 1H), 7.16 (d, J=3.5 Hz, 1H), 7.39 (m, 2H), 7.59 (m, 2H).

Sources & evidence

ORD record
ord-7a6d9776c88b4134abb211f1e26865f2
Source dataset
uspto-grants-2016_05
Patent number
US09340564B2

Reaction notes

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