HCID 67440895, compound → HCID 54575607, compound

HRID 2096288Notes

Reaction equation

HRID 2096288 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([CH2:8][C:9]2[CH:33]=[CH:32][C:12]([CH2:13][NH:14][CH:15]3[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OCC4C=CC=CC=4)[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)[N:4]2[CH:34]=[C:35]([C:37]3[C:45]4[C:40](=[N:41][CH:42]=[CH:43][CH:44]=4)[NH:39][CH:38]=3)[CH:36]=[C:3]12>FC(F)(F)C(O)=O>[NH2:21][CH:18]1[CH2:19][CH2:20][CH:15]([NH:14][CH2:13][C:12]2[CH:32]=[CH:33][C:9]([CH2:8][C:5]3[N:4]4[CH:34]=[C:35]([C:37]5[C:45]6[C:40](=[N:41][CH:42]=[CH:43][CH:44]=6)[NH:39][CH:38]=5)[CH:36]=[C:3]4[C:2](=[O:1])[NH:7][CH:6]=3)=[CH:10][CH:11]=2)[CH2:16][CH2:17]1

Participants

3

Reactant 1

HCID 67440895HCID 67440895, compound

Product 1

HCID 54575607HCID 54575607, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of EXAMPLE 44A (25 mg, 0.04 mmol) in trifluoroacetic acid (2 ml) was stirred at 50° C. for 3 hours. The reaction mixture was then concentrated, and the residue was purified by HPLC (0-100% gradient acetonitrile in water containing 0.1% trifluoroacetic acid) to afford the title compound. MS (DCI/NH3) m/z 467 (M+H)+; 1H NMR (300 MHz, dimethylsulfoxide-d6): δ 1.11-1.54 (m, 4H), 1.55-1.89 (m, 4H), 2.91-3.09 (m, 2H), 4.12 (d, J=4.41 Hz, 2H), 4.18 (s, 2H), 6.52 (d, J=5.76 Hz, 1H), 7.15 (dd, J=7.80, 4.75 Hz, 1H), 7.28 (d, J=1.70 Hz, 1H), 7.45 (d, J=8.81 Hz, 2H), 7.55 (d, J=8.81 Hz, 2H), 7.67 (d, J=1.36 Hz, 1H), 7.83 (d, J=2.37 Hz, 1H), 8.13 (d, J=7.80 Hz, 1H), 8.24 (s, 1H) 10.57 (d, J=5.42 Hz, 1H), 11.76 (s, 1H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. customthe residue was purified by HPLC (0-100% gradient acetonitrile in water containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-01a7d0df3f7040fabd83e1bfa811fb6e
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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