Acetic Acid → HCID 68507068, compound

HRID 1714054Notes

Reaction equation

HRID 1714054 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][NH:19][CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31]([OH:34])(=O)[CH3:32].CCN(C(C)C)C(C)C.[CH3:44][N:45]([C:47](ON1N=NC2C=CC=CC1=2)=[N+:48]([CH3:50])C)C.[B-](F)(F)(F)F>C(Cl)Cl>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:27]([O:29][CH3:30])=[O:28])=[CH:12][C:13]=3[N:14]3[CH2:21][CH2:20][N:19]([C:31](=[O:34])[CH2:32][N:48]4[CH:50]=[CH:44][N:45]=[CH:47]4)[CH2:18][C:17]4[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 68507183HCID 68507183, compound

Product 1

HCID 68507068HCID 68507068, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 eq of methyl-14-cyclohexyl-3-fluoro-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocin-11-carboxylate (prepared as described in Example 18, Step 5) in DCM (0.06 M), 1.1 eq of imidazo-1-yl acetic acid in DCM (0.05 M), 3 eq of DIPEA and 1.5 eq of TBTU were added and the mixture stirred at RT overnight. Volatiles were removed in vacuo and the crude material was used in the next step without further purification; MS (ES+) m/z 515 (M+H)+.

Workup

  1. customVolatiles were removed in vacuo
  2. customthe crude material was used in the next step without further purification

Sources & evidence

ORD record
ord-8ed147234c5e4616a1a2a781a6c2803d
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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