Trifluoroacetic acid → HCID 69585732, compound

HRID 722269Notes

Reaction equation

HRID 722269 reaction equation
C([O-])(=O)C.[K+].N[C@@H]1C2C(=CC=CC=2)C[C@H]1NC(C1NC2C(C=1)=CC(Cl)=CC=2)=O.C(O)(C(F)(F)F)=O.[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([C:46]([NH:48][C@@H:49]1[CH2:57][C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[C@H:50]1[NH:58][CH2:59][C@@H:60]1[CH2:64][O:63]C(C)(C)[O:61]1)=[O:47])=[CH:40]2>CO.C(Cl)Cl>[Cl:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41]([C:46]([NH:48][C@@H:49]1[CH2:57][C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[C@H:50]1[NH:58][CH2:59][C@@H:60]([OH:61])[CH2:64][OH:63])=[O:47])=[CH:40]2

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 517044Potassium AcetateHCID 58742475HCID 58742475, compoundHCID 69585659HCID 69585659, compound

Product 1

HCID 69585732HCID 69585732, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,3-O-(S)-Isopropylidene-L-glyceraldehyde (98 mg, 0.75 mmol) and potassium acetate (75 mg, 0.75 mmol) were added to a solution of N-{(1R,2R)-1-amino-2,3-dihydro-1H-inden-2-yl}-5-chloro-1H-indole-2-carboxamide (Method 5, 328 mg, 0.75 mmol) in MeOH (10 mL). The reaction was stirred at ambient temperature for approximately 5 mins then macroporous triethylammonium methyl polystyrene cyanoborohydride (352 mg, 0.9 mmol) was added and the reaction stirred at ambient temperature for a further 5 h. The reaction was then filtered and the volatiles were removed by evaporation under reduced pressure to 5-chloro-N-[(1R,2R)-1-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-2,3-dihydro-1H-inden-2-yl]-1H-indole-2-carboxamide which was used crude in the next stage. TFA (3 mL) was added to a solution of 5-chloro-N-[(1R,2R)-1-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-2,3-dihydro-1H-inden-2-yl]-1H-indole-2-carboxamide (100 mg, 0.23 mmol) in DCM (10 mL) and the reaction was stirred at ambient temperature for 24 h. The volatiles were removed by evaporation under reduced pressure to afford the title compound (90 mg, 100%) as a white solid.

Workup

  1. stirringthe reaction stirred at ambient temperature for a further 5 h
  2. filtrationThe reaction was then filtered
  3. customthe volatiles were removed by evaporation under reduced pressure to 5-chloro-N-[(1R,2R)-1-({[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl}amino)-2,3-dihydro-1H-inden-2-yl]-1H-indole-2-carboxamide which
  4. stirringthe reaction was stirred at ambient temperature for 24 h
  5. customThe volatiles were removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-6ca6acc30a034329af064c9cae3d2fa0
Source dataset
uspto-grants-2006_11
Patent number
US07138415B2

Reaction notes

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