Trifluoroacetic acid → HCID 68578802, compound

HRID 1970396Notes

Reaction equation

HRID 1970396 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]([C:23]#[C: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.C(O)(C(F)(F)F)=[O:37]>>[NH2:5][C:6]1[S:7][CH2:8][C@:9]2([N:35]=1)[C:10]1[CH:11]=[C:12]([C:29]3[CH:30]=[N:31][CH:32]=[N:33][CH:34]=3)[CH:13]=[CH:14][C:15]=1[O:16][C:17]1[C:22]2=[CH:21][C:20]([C:23](=[O:37])[CH2:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67247364HCID 67247364, compound

Product 1

HCID 68578802HCID 68578802, compound

Conditions

Temperature
160 °C

Procedure

A resealable tube charged with N-tert-butyl-2′-(3,3-dimethylbut-1-ynyl)-7′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthen]-2-amine (0.113 g, 0.234 mmol) and TFA (2 mL) was sealed and heated to 160° C. After 3 hrs, the solvent was removed in vacuo and the residue taken up in 2 mL DCM. TEA (ca. 0.1 mL) was added and the solution was loaded onto a silica gel plug and purified by silica gel chromatography using 2-4% MeOH:DCM w/1% NH4OH to afford crude, racemic product that was resolved by chiral column chromatography to give both (R) and (S)-1-(2-amino-2′-(pyrimidin-5-yl)-5H-spiro[thiazole-4,9′-xanthene]-7′-yl)-3,3-dimethylbutan-1-one. MS Found: MH+=445.2.

Workup

  1. customwas sealed
  2. customthe solvent was removed in vacuo
  3. additionTEA (ca. 0.1 mL) was added
  4. custompurified by silica gel chromatography
  5. customto afford crude, racemic product that

Sources & evidence

ORD record
ord-3ad1168e0ce1433da003f35a47af3c89
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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