Trifluoroacetic acid → 3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-aminohexanoate

HRID 1422501Notes

Reaction equation

HRID 1422501 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH:28][C:29]1[N:37]=[C:36]([C:38]2[C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[S:41][CH:42]=2)[N:35]=[C:34]2[C:30]=1[N:31]=[CH:32][N:33]2[CH:47]([CH3:49])[CH3:48])=[O:15])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH2:26][CH2:27][NH:28][C:29]1[N:37]=[C:36]([C:38]2[C:39]3[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=3[S:41][CH:42]=2)[N:35]=[C:34]2[C:30]=1[N:31]=[CH:32][N:33]2[CH:47]([CH3:49])[CH3:48])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 594089113-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-(tert-butoxycarbonylamino)hexanoate

Product 1

HCID 594089403-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-aminohexanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(2-(2-(benzo[b]thiophen-3-yl)-9-isopropyl-9H-purin-6-ylamino)ethyl)-1H-indol-5-yl 6-(tert-butoxycarbonylamino)hexanoate (a) (80 mg, 0.117 mmol) in DCM (20 ml) was added TFA (5 ml). The reaction was stirred at rt for 3 hr. It was concentrated. Aqueous sodium carbonate solution was added and the mixture was extracted with DCM. The organic fractions were combined, dried over sodium sulfate, and concentrated to afford the product as an oil. MS m/z 582.2 (M+1).

Workup

  1. concentrationIt was concentrated
  2. additionAqueous sodium carbonate solution was added
  3. extractionthe mixture was extracted with DCM
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-248723e2bcf049b3b31caef857191e00
Source dataset
uspto-grants-2015_01
Patent number
US08927281B2

Reaction notes

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