Trifluoroacetic acid → HCID 59735859, compound

HRID 2113216Notes

Reaction equation

HRID 2113216 reaction equation
[C:1]([C:3]1[CH:47]=[CH:46][CH:45]=[CH:44][C:4]=1[CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:31]=[C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[C:42]#[N:43])[CH:33]=1)[C:10]([NH:12][C:13]1[N:18]=[CH:17][C:16]([N:19]([CH2:27][CH2:28][O:29][CH3:30])C(=O)OC(C)(C)C)=[CH:15][CH:14]=1)=[O:11])#[N:2].FC(F)(F)C(O)=O>ClCCl>[C:42]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[CH2:35][O:34][C:32]1[CH:31]=[C:9]([CH:8]=[C:7]([O:6][CH2:5][C:4]2[CH:44]=[CH:45][CH:46]=[CH:47][C:3]=2[C:1]#[N:2])[CH:33]=1)[C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([NH:19][CH2:27][CH2:28][O:29][CH3:30])=[CH:17][N:18]=1)=[O:11])#[N:43]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67162766HCID 67162766, compound

Product 1

HCID 59735859HCID 59735859, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 6-({3,5-di(2-cyanobenzyloxy)benzoyl}amino)pyridin-3-yl(2-methoxyethyl)carbamate (237 mg) in dichloromethane (10 ml) was added trifluoroacetic acid (3 ml). The solution was stirred at ambient temperature for three hours. Volatile material was removed by evaporation. The residue was diluted in DCM (100 ml), washed with 2M sodium Hydroxide (50 ml), brine (50 ml), dried over MgSO4. Volatile material was removed by evaporation to give the title compound (190 mg) as a foam, 1H NMR δ (d6-DMSO): 3.22 (t, 2H), 3.28 (2, 3H), 3.50 (t, 2H), 5.31 (s, 4H), 6.92 (s, 1H), 7.12 (dd, 1H), 7.34 (s, 2H), 7.57 (m, 2H), 7.75 (m, 5H), 7.82 (d, 1H), 7.91 (d, 2H), 10.49 (br s, 1H). MS ES+ 534.41 (M+H)+.

Workup

  1. customVolatile material was removed by evaporation
  2. additionThe residue was diluted in DCM (100 ml)
  3. washwashed with 2M sodium Hydroxide (50 ml), brine (50 ml)
  4. dry with materialdried over MgSO4
  5. customVolatile material was removed by evaporation

Sources & evidence

ORD record
ord-a8f91a1fe9da4c78bc2d5982f9e55f2b
Source dataset
uspto-grants-2009_04
Patent number
US07524957B2

Reaction notes

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