Trifluoroacetic acid → HCID 87315714, compound

HRID 624398Notes

Reaction equation

HRID 624398 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:9]=2[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:24]=[CH:25][C:26]([C:49](=[O:71])[NH:50][S:51]([C:54]4[CH:59]=[CH:58][C:57]([NH:60][CH2:61][CH:62]5[CH2:67][CH2:66][O:65][CH2:64][CH2:63]5)=[C:56]([N+:68]([O-:70])=[O:69])[CH:55]=4)(=[O:53])=[O:52])=[C:27]([CH:48]=3)[O:28][C:29]3[CH:30]=[C:31]4[C:35](=[CH:36][CH:37]=3)[NH:34][CH:33]=[C:32]4[CH2:38][CH2:39][NH:40]C(=O)OC(C)(C)C)[CH2:19][CH2:18]2)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[NH2:40][CH2:39][CH2:38][C:32]1[C:31]2[C:35](=[CH:36][CH:37]=[C:29]([O:28][C:27]3[CH:48]=[C:23]([N:20]4[CH2:21][CH2:22][N:17]([CH2:16][C:9]5[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:8]=5[C:5]5[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=5)[CH2:18][CH2:19]4)[CH:24]=[CH:25][C:26]=3[C:49]([NH:50][S:51]([C:54]3[CH:59]=[CH:58][C:57]([NH:60][CH2:61][CH:62]4[CH2:63][CH2:64][O:65][CH2:66][CH2:67]4)=[C:56]([N+:68]([O-:70])=[O:69])[CH:55]=3)(=[O:53])=[O:52])=[O:71])[CH:30]=2)[NH:34][CH:33]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87398002HCID 87398002, compound

Product 1

HCID 87315714HCID 87315714, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 299E (146.6 mg) in dichloromethane (10 mL) was cooled in an ice bath and 2,2,2-trifluoroacetic acid (5 mL) was added dropwise over 5 minutes. The reaction mixture was stirred 15 minutes under nitrogen, the ice bath was removed and the reaction was allowed to come to ambient temperature. The reaction was stirred 1.5 hours and then concentrated. The crude material was purified by reverse phase chromatography with ammonium acetate buffer in acetonitrile to give the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ 10.86 (d, 1H), 8.39 (d, 1H), 8.33 (t, 1H), 8.06 (br s, 1H), 7.71 (dd, 1H), 7.53 (d, 1H), 7.34 (d, 2H), 7.26 (d, 1H), 7.19 (d, 1H), 7.05 (m, 3H), 6.89 (d, 1H), 6.70 (dd, 1H), 6.52 (dd, 1H), 6.15 (d, 1H), 3.83 (dd, 2H), 3.22 (m, 3H), 2.82-3.00 (m, 8H), 2.72 (s, 2H), 2.16 (m, 6H), 1.96 (s, 2H), 1.88 (m, 4H), 1.60 (d, 2H), 1.38 (m, 2H), 1.24 (m, 2H), 0.93 (s, 6H).

Workup

  1. customthe ice bath was removed
  2. customto come to ambient temperature
  3. stirringThe reaction was stirred 1.5 hours
  4. concentrationconcentrated
  5. customThe crude material was purified by reverse phase chromatography with ammonium acetate buffer in acetonitrile

Sources & evidence

ORD record
ord-2b4367569c7a434cbc24ff3c627a1f33
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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