Toluene → HCID 86698430, compound

HRID 527573Notes

Reaction equation

HRID 527573 reaction equation
CC([N:5]([C@@:9]([CH3:33])([C:12]([NH:14][C:15]1[CH:16]=[N:17][C:18]([O:21][C:22]2[C:27]3[C:28]4([CH2:31][O:32][C:26]=3[CH:25]=[CH:24][CH:23]=2)[CH2:30][CH2:29]4)=[CH:19][CH:20]=1)=[O:13])[CH2:10][CH3:11])C(=O)[O-])(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>ClCCl>[C:28]12([C:27]3[C:22]([O:21][C:18]4[N:17]=[CH:16][C:15]([NH:14][C:12](=[O:13])[C@:9]([CH3:33])([CH2:10][CH3:11])[NH2:5])=[CH:20][CH:19]=4)=[CH:23][CH:24]=[CH:25][C:26]=3[O:32][CH2:31]1)[CH2:29][CH2:30]2

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 86698431HCID 86698431, compound2×

Product 1

HCID 86698430HCID 86698430, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl[(1R)-1-methyl-1-({[6-(spiro[1-benzofuran-3,1′-cyclopropan]-4-yloxy)-3-pyridinyl]amino}carbonyl)propyl]carbamate (Intermediate 92, 106 mg) in dry dichloromethane (2 ml) at 0° C. TFA (0.360 ml, 4.67 mmol) was added. The mixture was stirred at this temperature for 5 minutes, then allowed to warm up at room temperature. After 2 hours UPLC/MS showed the absence of the starting material and the presence of the desired compound: toluene (5 ml) was added and the mixture was concentrated under vacuum. The residue was loaded on a SCX cartridge (1 g), which was eluted with methanol and a 1M NH3 solution in methanol. The basic eluate was concentrated under vacuum to afford the title compound as a brown oil (68 mg) which was used in the following experiment without further purification.

Workup

  1. customat 0° C
  2. waitAfter 2 hours UPLC/MS showed

Sources & evidence

ORD record
ord-fd9c7cee2ffa46d78c15cbdbe5c4d078
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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