Hydrogen Bromide → HCID 67240351, compound

HRID 335802Notes

Reaction equation

HRID 335802 reaction equation
C([NH:5][C:6]1[S:7][CH2:8][C:9]2([N:35]=1)[C:22]1[CH:21]=[C:20]([O:23][CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:19]=[CH:18][C:17]=1[O:16][C:15]1[C:10]2=[CH:11][C:12]([C:29]2[CH:30]=[N:31][CH:32]=[N:33][CH:34]=2)=[CH:13][CH:14]=1)(C)(C)C.Br>>[CH2:24]([O:23][C:20]1[CH:19]=[CH:18][C:17]2[O:16][C:15]3[C:10](=[CH:11][C:12]([C:29]4[CH:30]=[N:31][CH:32]=[N:33][CH:34]=4)=[CH:13][CH:14]=3)[C@@:9]3([CH2:8][S:7][C:6]([NH2:5])=[N:35]3)[C:22]=2[CH:21]=1)[C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 67242092HCID 67242092, compound

Product 1

HCID 67240351HCID 67240351, compound

Conditions

Temperature
80 °C

Procedure

A resealable tube charged with a solution of N-tert-butyl-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine (0.033 g, 0.068 mmol) in 48% HBr (1.00 mL, 18.42 mmol) was heated to 80° C. After 3 hrs, the solution was cooled and evaporated to dryness with a stream of N2. The residue was treated with CH2Cl2 (2 mL) and TEA (0.1 mL). The solution was loaded onto a silica gel column and purified with 1-5% MeOH:CH2Cl2 w/1% NH4OH (Rf=0.5 in 10% MeOH:CH2Cl2 w/1% NH4OH) to afford racemic material that was resolved by chiral chromatography to give both (R) and (S)-2′-(neopentyloxy)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine MS Found: MH+=433.2.

Workup

  1. temperaturethe solution was cooled
  2. customevaporated to dryness with a stream of N2
  3. additionThe residue was treated with CH2Cl2 (2 mL) and TEA (0.1 mL)
  4. custompurified with 1-5% MeOH
  5. customto afford racemic material that

Sources & evidence

ORD record
ord-c11f83b52e834bde8e8b2ae79d8f017f
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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