1,3-Thiazole-2-carbaldehyde → HCID 11726186, compound

HRID 1791378Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][O:17][CH2:16][CH2:15][NH:14]3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:18][O:17][CH2:16][CH2:15][N:14]3[CH2:24][C:20]3[S:19][CH:23]=[CH:22][N:21]=3)[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Reactant 3

HCID 27349031,3-Thiazole-2-carbaldehyde

HCID 5049666Sodium triacetoxyborohydride

HCID 22032773HCID 22032773, compound

Product 1

HCID 11726186HCID 11726186, compound

Procedure

3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-4-pyridin-2-ylmethyl-morpholine was obtained as described in Example 43 from (48 mg, 44%) 3-[3-(3-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-morpholine (80 mg, 0.30 mmol) with 2-thiazolecarboxaldehyde (68 mg, 0.60) and sodium triacetoxyborohydride (89 mg, 0.42 mmol). The product was purified by SPE chromatography on silica gel using 20–60% ethyl acetate in hexanes. 1H NMR (CDCl3), δ(ppm): 8.13 (s, 1H), 8.01 (d, 1H), 7.75 (d, 1H), 7.47 (m, 2H), 7.33 (d, 1H), 4.29 (m, 1H), 4.15 (m, 4H), 3.88 (m, 2H), 3.30 (m, 1H), 2.70 (m, 1H).

Workup

customThe product was purified by SPE chromatography on silica gel using 20–60% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-1b5bd9a23d704fe3a036863bea719c8b
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074809B2

Reaction notes

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