4-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methylbenzaldehyde → HCID 56597274, compound

HRID 1035245Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:19][CH:18]([O:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[C:23]([CH3:29])[CH:22]=4)[CH2:17]3)=[O:15])=[N:11][N:10]=2)=[CH:5][CH:4]=1.FC(F)(F)C(O)=O.[CH2:37]([C:39]1([OH:43])[CH2:42][NH:41][CH2:40]1)[CH3:38]>>[CH2:37]([C:39]1([OH:43])[CH2:42][N:41]([CH2:25][C:24]2[CH:27]=[CH:28][C:21]([O:20][CH:18]3[CH2:19][N:16]([C:14]([C:12]4[O:13][C:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)=[N:10][N:11]=4)=[O:15])[CH2:17]3)=[CH:22][C:23]=2[CH3:29])[CH2:40]1)[CH3:38]

Participants

Reactant 2

HCID 580431564-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)-2-methylbenzaldehyde

HCID 666534471354792-80-5

Product 1

HCID 56597274HCID 56597274, compoundYield 41%

Procedure

Using a similar protocol as described in Example 70 employing 73C and 70A as starting materials afforded 100 mg (41%) of 73 as a solid. 1H NMR (500 MHz, CDCl3): δ 0.98 (t, 3H), 1.80 (q, 2H), 2.30 (s, 3H), 2.98 (m, 2H), 3.33 (d, 2H), 3.57 (s, 2H), 3.89 (s, 3H), 4.32 (m, 1H), 4.63 (m, 1H), 4.73 (m, 1H), 5.05 (m, 1H), 5.11 (m, 1H), 6.54 (d, 1H), 6.59 (s, 1H), 7.03 (d, 2H), 7.16 (d, 1H), 8.10 (d, 2H), MS (APCI+) m/z 479 [M+H]+, LC purity: 96%.

Sources & evidence

ORD record: ord-70a6f80daca64c45a59ba77261cf5f53
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546375B2

Reaction notes

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