Water → HCID 59463930, compound

HRID 2387643Notes

Reaction equation

HRID 2387643 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-73ede14b860d4544a558a3231da31c72
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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