L-Proline → 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-proline

HRID 1942758Notes

Reaction equation

HRID 1942758 reaction equation
[CH2:1]([C:3]1[C:8]([CH2:9][CH:10]=O)=[CH:7][CH:6]=[CH:5][C:4]=1[C:12]1[N:16]=[C:15]([C:17]2[CH:18]=[CH:19][C:20]([CH2:25][CH:26]([CH3:28])[CH3:27])=[C:21]([CH:24]=2)[C:22]#[N:23])[S:14][N:13]=1)[CH3:2].[NH:29]1[CH2:36][CH2:35][CH2:34][C@H:30]1[C:31]([OH:33])=[O:32].C([BH3-])#N.[Na+]>C(O)C>[C:22]([C:21]1[CH:24]=[C:17]([C:15]2[S:14][N:13]=[C:12]([C:4]3[C:3]([CH2:1][CH3:2])=[C:8]([CH2:9][CH2:10][N:29]4[CH2:36][CH2:35][CH2:34][C@H:30]4[C:31]([OH:33])=[O:32])[CH:7]=[CH:6][CH:5]=3)[N:16]=2)[CH:18]=[CH:19][C:20]=1[CH2:25][CH:26]([CH3:28])[CH3:27])#[N:23]

Participants

5

Reactant 3

HCID 145742L-ProlineHCID 5003444Sodium cyanoborohydrideHCID 58494132HCID 58494132, compound

Product 1

HCID 545784641-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-prolineYield 15.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-{3-[2-ethyl-3-(2-oxoethyl)phenyl]-1,2,4-thiadiazol-5-yl}-2-(2-methylpropyl)benzonitrile (D62) (100 mg, 0.257 mmol) and L-proline (59.1 mg, 0.513 mmol) stirred in Ethanol (10 mL) for 20 min was added sodium cyanoborohydride (48.4 mg, 0.770 mmol). This mixture was stirred at room temperature for 2 h. The reaction was quenched with water, then dried and dissolved in DMF. The residue was purified by for Mass Directed AutoPrep to afford 1-[2-(3-{5-[3-cyano-4-(2-methylpropyl)phenyl]-1,2,4-thiadiazol-3-yl}-2-ethylphenyl)ethyl]-L-proline (E76) (20 mg) as a TFA salt (white solid).

Workup

  1. customThe reaction was quenched with water
  2. customdried
  3. dissolutiondissolved in DMF
  4. customThe residue was purified by for Mass Directed AutoPrep

Sources & evidence

ORD record
ord-f43a625880cc48a1b46503d94fa27b9e
Source dataset
uspto-grants-2013_03
Patent number
US08389508B2

Reaction notes

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