Water → HCID 59463930, compound

HRID 2040390Notes

Reaction equation

HRID 2040390 reaction equation
[Si]([O:18][CH2:19][CH2:20][C:21]1([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[N:25]([C:26]2[S:27][C:28]3[CH2:29][N:30](C(OC(C)(C)C)=O)[CH2:31][CH2:32][C:33]=3[N:34]=2)[N:24]=[C:23]([C:42]2[CH:47]=[C:46]([F:48])[CH:45]=[CH:44][C:43]=2[F:49])[S:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.O1CCOCC1.O>O1CCOCC1>[F:49][C:43]1[CH:44]=[CH:45][C:46]([F:48])=[CH:47][C:42]=1[C:23]1[S:22][C:21]([CH2:20][CH2:19][OH:18])([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[N:25]([C:26]2[S:27][C:28]3[CH2:29][NH:30][CH2:31][CH2:32][C:33]=3[N:34]=2)[N:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 204431481,4-Dioxane hydrochloride2×HCID 68503233HCID 68503233, compound

Product 1

HCID 59463930HCID 59463930, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl 2-(2-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (prepared according to Example 26, Steps A-D; 0.090 g, 0.113 mmol) in 1 mL of 1,4-dioxane was added 4M HCl/dioxane (1 mL). The mixture was stirred at room temperature for 16 hours then treated with 4M HCl/dioxane (2 mL) and stirred for a further 3 hours. Water (1 mL) was added and the mixture was stirred for 16 hours then concentrated and dried in vacuo. The residue was triturated with diethyl ether, filtered, washed with ether and dried in vacuo to afford the desired product as an orange/yellow solid, 0.023 g, 38%. MS ESI (+) m/z 459 (M+1) detected; 1H NMR (400 MHz, CDCl3) δ 7.59 (m, 1H), 7.46 (m, 2H), 7.33 (m, 3H), 7.07 (m, 2H), 4.12 (m, 1H), 3.95 (m, 1H), 3.87 (m, 2H), 3.65 (m, 2H), 3.05 (m, 2H), 2.84 (m, 1H), 2.43 (m, 2H) ppm.

Workup

  1. stirringstirred for a further 3 hours
  2. stirringthe mixture was stirred for 16 hours
  3. concentrationthen concentrated
  4. customdried in vacuo
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered
  7. washwashed with ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-19a4b78fcd9743cd8e066f6aff7e2b74
Source dataset
uspto-grants-2013_11
Patent number
US08580828B2

Reaction notes

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