HCID 69263041, compound → HCID 16041243, compound

HRID 2366471Notes

Reaction equation

HRID 2366471 reaction equation
[C:1]([C:4]1[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][CH2:22][N:21](C(OCC5C=CC=CC=5)=O)[CH2:20]4)=[CH:15][C:14]=3[F:35])[NH:9][C:8]=2[CH:7]=[C:6]([F:36])[CH:5]=1)(=[O:3])[NH2:2]>C(O)(C(F)(F)F)=O>[F:36][C:6]1[CH:5]=[C:4]([C:1]([NH2:2])=[O:3])[C:12]2[N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([CH:19]4[CH2:24][CH2:23][CH2:22][NH:21][CH2:20]4)=[CH:15][C:14]=3[F:35])[NH:9][C:8]=2[CH:7]=1

Participants

3

Reactant 1

HCID 69263041HCID 69263041, compound

Product 1

HCID 16041243HCID 16041243, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 59D (150 mg) in TFA (10 mL) at 40° C. was stirred for 2.5 days and concentrated. The concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient). 1H NMR (CD3OD) δ 1.83-1.96 (m, 2H), 2.07-2.15 (m, 2H), 3.02-3.21 (m, 3H), 3.44-3.54 (m, 2H), 7.32 (dd, J=4.14, 1.69 Hz, 1H), 7.35 (s, 1H), 7.50 (dd, J=8.29, 2.45 Hz, 1H), 7.69 (dd, J=10.43, 2.45 Hz, 1H), 8.30 (t, J=7.98 Hz, 1H).

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by HPLC (Zorbax, C-18, 250×2.54 column, Mobile phase A: 0.1% TFA in water; B: 0.1% TFA in CH3CN; 0-100% gradient)

Sources & evidence

ORD record
ord-c4b3a95f52eb46b9be4f94fd2aea77ec
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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