(2S)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acid → (2S)-N-[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]-6-iodo-3,4-dihydro-2H-chromene-2-carboxamide

HRID 896865Notes

Reaction equation

HRID 896865 reaction equation
[I:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[O:8][C@H:7]([C:12]([OH:14])=O)[CH2:6][CH2:5]2.Cl.Cl.[NH2:17][CH2:18][C@@H:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[OH:20]>>[OH:20][C@H:19]([C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)[CH2:18][NH:17][C:12]([C@@H:7]1[CH2:6][CH2:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([I:1])[CH:3]=2)[O:8]1)=[O:14]

Participants

3

Reactant 2

HCID 59118151(2S)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acidHCID 69103521(1R)-2-amino-1-(3-pyridyl)ethanol dihydrochloride

Product 1

HCID 59118134(2S)-N-[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]-6-iodo-3,4-dihydro-2H-chromene-2-carboxamideYield 87%

Procedure

Using the same procedure described in Method A, using (2S)-6-iodo-3,4-dihydro-2H-chromene-2-carboxylic acid (Example 7, Method B) and (1R)-2-amino-1-(3-pyridinyl)ethanol dihydrochloride (U.S. Pat. No. 6,051,586), the title compound was obtained as a white solid in 87% yield. 1H NMR (DMSO-d6) δ 8.47 (d, J=2.2 Hz, 1 H), 8.43 (dd, J=6.6, 1.8 Hz, 1 H), 7.90 (t, J=7.1 Hz, 1 H), 7.69-7.60 (m, 1 H), 7.40-7.37 (m, 2 H), 7.30-7.26 (m, 1 H), 6.66 (d, J=9.1 Hz, 1 H), 5.66 (d, J=4.6 Hz, 1 H), 4.72 (q, J=5.0 Hz, 1 H), 4.52 (dd, J=8.3, 3.3 Hz, 1 H), 4.12 (dd, J=6.1, 1.8 Hz, 1 H), 3.36-3.32 (m, 1 H), 2.77-2.65 (m, 1 H), 2.58-2.52 (m, 1 H), 2.08-2.00 (m, 1 H), 1.85-1.73 (m, 1 H). LC-MS m/z 425.1 (MH+), RT=2.07 minutes.

Sources & evidence

ORD record
ord-accb050219714305bbd2abc1d4da8753
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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