HCID 90413388, compound → HCID 90413566, compound

HRID 1522043Notes

Reaction equation

HRID 1522043 reaction equation
[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:23][C:24]([CH:26]4[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)=[CH:25][C:18]=23)=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[N:6][CH:7]=1>ClCCl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:23][C:24]([CH:26]4[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]4)=[CH:25][C:18]=23)=[CH:4][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=2)=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 90413388HCID 90413388, compound

Product 1

HCID 90413566HCID 90413566, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of Example 307B (50 mg, 0.09 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (1 mL) was stirred for 15 minutes and concentrated. The residue was purified by reverse phase chromatography (C18 column) eluting with 10%-70% acetonitrile in 0.1% TFA water solution to provide the title compound. 1H NMR (400 MHz, DMSO-d6) δ 1.69-1.86 (m, 2H), 2.21 (d, 2H), 2.96-3.13 (m, 3H), 3.37 (d, 2H), 4.53 (s, 3H), 5.96 (s, 1H), 6.63 (s, 1H), 7.02 (d, 1H), 7.04-7.12 (m, 1H), 7.12-7.23 (m, 2H), 7.34-7.42 (m, 1H), 7.51 (s, 1H), 8.15 (s, 1H), 8.24 (d, 1H), 8.26-8.39 (m, 1H), 8.66 (d, 1H), 11.89 (s, 1H), LCMS: 436 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by reverse phase chromatography (C18 column)
  3. washeluting with 10%-70% acetonitrile in 0.1% TFA water solution

Sources & evidence

ORD record
ord-1486140682db4435a5dca5e90b3731e6
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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