Hydrochloride methanol → 3-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine

HRID 1713446Notes

Reaction equation

HRID 1713446 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=[C:9]([C:22]2[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=2[F:29])[S:8]1)=[N+]=[N-].Cl.CO>CO.[Pd]>[F:29][C:23]1[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=1[C:9]1[S:8][C:7]([CH2:6][CH2:5][CH2:4][NH2:1])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16]([CH3:21])[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=1

Participants

5

Reactant 2

HCID 21893726Hydrochloride methanolHCID 866087732-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

Product 1

HCID 119599503-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amineYield 61.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine (0.046 g, 0.090 mmol) in 2 mL of methanol was added 1N HCl/MeOH (0.27 mL, 0.27 mmol) followed by 10% Pd/C (10 mg). The mixture was hydrogenated under a balloon atmosphere for 1 hour then filtered through GF paper and the filtrate concentrated in vacuo. The residue was triturated with diethyl ether, filtered, washed with ether and dried in vacuo to afford the desired product as a bright yellow solid (0.027 g, 50%). MS ESI (+) m/z 486 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 1H), 7.45 (d, 2H, J=7.6 Hz), 7.32 (m, 2H), 7.26 (m, 1H), 7.06 (m, 2H), 3.50 (m, 2H), 3.43 (m, 1H), 2.77 (t, 2H, J=6.9 Hz), 2.68 (m, 2H), 2.56 (m, 2H), 2.46 (s, 3H), 2.41 (m, 1H), 1.99 (m, 1H), 1.55 (m, 1H) ppm.

Workup

  1. filtrationthen filtered through GF paper
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washwashed with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-510a6c48a0f644ac8a428c3683cafb41
Source dataset
uspto-grants-2010_09
Patent number
US07795282B2

Reaction notes

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