2-(3-Formylphenoxy)acetic acid → HCID 178513996, compound

HRID 592090Notes

Reaction equation

HRID 592090 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([NH:9][C@@H:10]2[C@@H:15]3[CH2:16][C@@H:12]([CH:13]=[CH:14]3)[C@@H:11]2[C:17]([NH2:19])=[O:18])[C:5]([Cl:20])=[CH:4][N:3]=1.[CH:21]([C:23]1[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=1)[O:26][CH2:27][C:28]([OH:30])=[O:29])=O>>[C:17]([C@H:11]1[C@H:12]2[CH2:16][C@H:15]([CH:14]=[CH:13]2)[C@H:10]1[NH:9][C:6]1[C:5]([Cl:20])=[CH:4][N:3]=[C:2]2[NH:1][C:21]([C:23]3[CH:24]=[C:25]([CH:31]=[CH:32][CH:33]=3)[O:26][CH2:27][C:28]([OH:30])=[O:29])=[N:8][C:7]=12)(=[O:18])[NH2:19]

Participants

3

Reactant 2

HCID 6018952-(3-Formylphenoxy)acetic acidHCID 117701912(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide

Product 1

HCID 178513996HCID 178513996, compoundYield 31%

Procedure

(1S,2S,3R,4R)-3-(2,3-Diamino-5-chloro-pyridin-4-ylamino)-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid amide (1 eq.) and 2-(3-Formylphenoxy)acetic acid (48) (1.1 eq) were reacted in an analogous manner as compound CCXXIII to yield the desired product (31%) as a brown solid. NMR: δ (1H, 400 MHz, DMSO-d6): 1.38 (1H, d, J=8.8 Hz), 2.23 (1H, d, J=8.4 Hz), 2.63 (1H, d, J=8 Hz), 2.78-2.88 (2H, m), 4.26 (2H, s), 5.20 (1H, t, J=8.4 Hz), 6.36-6.42 (2H, m), 6.90 (1H, d, J=8.8 Hz), 7.14 (1H, d, J=8.8 Hz), 7.21 (1H, bs), 7.36 (1H, t, J=7.2 Hz), 7.60-7.70 (2H, m), 7.78 (1H, s), 7.94 (1H, s).

Sources & evidence

ORD record
ord-272e94a9791a43f49b51657a6fc1eb10
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

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