1,3,4-Thiadiazol-2-amine → HCID 86637650, compound

HRID 1514080Notes

Reaction equation

HRID 1514080 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])=[CH:4][CH:3]=1.Cl.CN(C)CCCN=C=NCC.[S:33]1[CH:37]=[N:36][N:35]=[C:34]1[NH2:38].C(N(C(C)C)CC)(C)C>CC#N>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]([CH3:14])([CH3:13])[C:10]([NH:38][C:34]2[S:33][CH:37]=[N:36][N:35]=2)=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 199091,3,4-Thiadiazol-2-amineHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59138622HCID 59138622, compound

Product 1

HCID 86637650HCID 86637650, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-(6-chloro-pyridin-3-yl)-2,2-dimethyl-3-phenyl-propionic acid (Preparation 4, 100 mg, 0.345 mmol), 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDC) (132 mg, 0.69 mmol) and 1-hydroxy-7-benzotriazole (HOBt) (93 mg, 0.69 mmol), 1,3,4-thiadiazol-2-amine (103 mg, 1.04 mmol) and diisopropylethyl amine (0.21 ml, 1.21 mmol) in CH3CN (1 mL) was heated at 75° C. for 12 hours. The reaction mixture was filtered, concentrated and purified by silica gel flash chromatography using 50% ethyl acetate in hexanes to give 3-(6-chloro-pyridin-3-yl)-2,2-dimethyl-3-phenyl-N-[1,3,4]thiadiazol-2-yl-propionamide as a white solid. (102 mg, 79.3% yield).). 1H NMR (400 MHz, CDCl3): δ 1.31 (s, 3H), 1.32 (s, 3H), 4.57 (s, 1H), 7.15 (m, 1H), 7.20 (m, 2H), 7.28 (m, 3H), 7.85 (m, 1H), 8.26 (br s, 1H), 8.90 (s, 1H). LC/MS (m/z) 373.19 [(M+H)+]; HPLC Rt: 2.913 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel flash chromatography

Sources & evidence

ORD record
ord-d760add0f9af49258188b1656ecc616c
Source dataset
uspto-grants-2012_07
Patent number
US08222247B2

Reaction notes

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