Trifluoroacetic acid → HCID 71285244, compound

HRID 1481807Notes

Reaction equation

HRID 1481807 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:12]=[C:11]([C:33]2[CH:41]=[C:40]3[C:36]([C:37]4[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][C:38]=4[NH:39]3)=[CH:35][CH:34]=2)[C:10]=1[CH2:53][CH3:54])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl.[SiH](C(C)C)(C(C)C)C(C)C>[CH2:26]([O:25][C:13]1[N:12]=[C:11]([C:33]2[CH:41]=[C:40]3[C:36]([C:37]4[CH2:45][CH2:44][NH:43][CH2:42][C:38]=4[NH:39]3)=[CH:35][CH:34]=2)[C:10]([CH2:53][CH3:54])=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:14]=1[C:15]([O:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71284568HCID 71284568, compound

Product 1

HCID 71285244HCID 71285244, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 138754Silane, tris(1-methylethyl)-Solvent

Procedure

To a solution of tert-butyl 7-(4,6-bis(benzyloxy)-5-(benzyloxycarbonyl)-3-ethylpyridin-2-yl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (130 mg, 0.18 mmol) in CH2Cl2 (0.3 mL) and TIPSH (0.3 mL) was added TFA (0.3 mL). The mixture was stirred at room temperature for 20 min. The solvents were removed and the residue was treated with 2N NH3 in MeOH (0.5 mL). The mixture was concentrated and chromatographed (0-5% 2N NH3 in MeOH/CH2Cl2) to give the title compound (111 mg, 99%) as a white solid.

Workup

  1. customThe solvents were removed
  2. additionthe residue was treated with 2N NH3 in MeOH (0.5 mL)
  3. concentrationThe mixture was concentrated
  4. customchromatographed (0-5% 2N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-bd221bfc277f42328d61639eff0b316b
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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