HCID 56646457, compound → HCID 56928736, compound

HRID 510077Notes

Reaction equation

HRID 510077 reaction equation
[NH2:1][C:2]1[C:7]([N:8]([CH2:13][CH:14]([F:16])[F:15])[C:9](=[O:12])OC)=[C:6]([NH2:17])[N:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:3]=1>O1CCCC1>[NH2:17][C:6]1[N:5]=[C:4]([C:18]2[C:26]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[N:19]=2)[N:3]=[C:2]2[C:7]=1[N:8]([CH2:13][CH:14]([F:16])[F:15])[C:9](=[O:12])[NH:1]2

Participants

3

Reactant 1

HCID 56646457HCID 56646457, compound

Product 1

HCID 56928736HCID 56928736, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

132 mg (0.279 mmol) of the compound prepared in example 12A were dissolved in tetrahydrofuran (8 ml), and 0.307 ml of a 1M solution of bis(trimethylsilyl)sodium amide in tetrahydrofuran were added at 0° C. Stirring of the mixture at RT was continued overnight. This was followed by concentration and purification of the residue by means of preparative HPLC (eluent: acetonitrile/water with 0.05% formic acid, gradient). 81 mg of the title compound were obtained (62% of theory).

Workup

  1. concentrationThis was followed by concentration and purification of the residue by means of preparative HPLC (eluent: acetonitrile/water with 0.05% formic acid, gradient)

Sources & evidence

ORD record
ord-5750f057411a4131919a686d5d15004c
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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