1,3-Thiazole-2-carbaldehyde → (S)-3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

HRID 1791376Notes

Reaction equation

HRID 1791376 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[N: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+]>ClC(Cl)C>[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[CH2:24][N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]1[O:10][N:9]=[C:8]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])[N:7]=1

Participants

5

Reactant 3

HCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69619317(S)-3-(5-Pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile

Product 1

HCID 11484507(S)-3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

3-[5-(1-Thiazol-2-ylmethyl-pyrrolidin-2-yl)-[1,2,4]oxadiazol-3-yl]-benzonitrile (63.5 mg, 91%) was obtained as described in Example 43 from (S)-3-(5-pyrrolidin-2-yl-[1,2,4]oxadiazol-3-yl)-benzonitrile (49.8 mg, 0.18 mmol) reacted with thiazole-2-carbaldehyde (35.2 mg, 0.31 mmol) and sodium triacetoxyborohydride (72 mg, 0.34 mmol) is in dichloroethane (3 mL) at room temperature. 1H NMR (CDCl3), δ(ppm): 8.39 (s, 1H), 8.32 (d, 1H), 7.78 (d, 1H), 7.68 (d, 1H), 7.60 (t, 1H), 7.27 (d, 1H), 4.32 (dd, 1H), 4.27 (dab, 1H), 4.17 (dab, 1H), 3.31 (m, 1H), 2.81 (q, 1H), 2.39 (m, 1H), 2.25 (m, 1H), 2.14 (m, 1H), 2.04 (m, 1H).

Sources & evidence

ORD record
ord-e854f20d87a8459eb201cbef7ecd8e22
Source dataset
uspto-grants-2006_07
Patent number
US07074809B2

Reaction notes

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