Trifluoroacetic acid → HCID 67225245, compound

HRID 629643Notes

Reaction equation

HRID 629643 reaction equation
COC1C=CC(C(C2C=CC(OC)=CC=2)[N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C:20]4[CH:48]=[C:47]([N:49]5[CH2:54][CH2:53][N:52]([CH2:55][C:56]6[CH2:61][CH2:60][C:59]([CH3:63])([CH3:62])[CH2:58][C:57]=6[C:64]6[CH:69]=[CH:68][C:67]([Cl:70])=[CH:66][CH:65]=6)[CH2:51][CH2:50]5)[CH:46]=[CH:45][C:21]=4[C:22]([NH:24][S:25]([C:28]4[CH:33]=[CH:32][C:31]([NH:34][CH2:35][CH:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)=[C:30]([N+:42]([O-:44])=[O:43])[CH:29]=4)(=[O:27])=[O:26])=[O:23])[C:13]=3[N:12]=[CH:11]2)=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[C:18]([O:19][C:20]3[CH:48]=[C:47]([N:49]4[CH2:50][CH2:51][N:52]([CH2:55][C:56]5[CH2:61][CH2:60][C:59]([CH3:62])([CH3:63])[CH2:58][C:57]=5[C:64]5[CH:65]=[CH:66][C:67]([Cl:70])=[CH:68][CH:69]=5)[CH2:53][CH2:54]4)[CH:46]=[CH:45][C:21]=3[C:22]([NH:24][S:25]([C:28]3[CH:33]=[CH:32][C:31]([NH:34][CH2:35][CH:36]4[CH2:41][CH2:40][O:39][CH2:38][CH2:37]4)=[C:30]([N+:42]([O-:44])=[O:43])[CH:29]=3)(=[O:27])=[O:26])=[O:23])[C:13]=2[N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 87441736HCID 87441736, compound

Product 1

HCID 67225245HCID 67225245, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 403H (174 mg) and dichloromethane (25 mL) was cooled in an ice bath and 2,2,2-trifluoroacetic acid (25 mL) was added slowly dropwise. The reaction mixture was stirred 30 minutes under nitrogen and the ice bath was removed. The reaction was stirred 18 hours and then concentrated. The crude product was purified by reverse phase chromatography with ammonium acetate buffer in acetonitrile to give the title compound. 1H NMR (400 MHz, pyridine-d5) δ 9.30 (d, 1H), 8.69 (t, 1H), 8.59 (s, 1H), 8.42 (dd, 1H), 7.99 (d, 1H), 7.53 (d, 1H), 7.43 (d, 2H), 7.26 (m, 1H), 7.18 (m, 1H), 7.06 (d, 2H), 6.94 (d, 1H), 6.72-6.66 (m, 2H), 5.53 (m, 2H), 3.98 (m, 2H), 3.32 (m, 2H), 3.18 (t, 2H), 2.03 (m, 4H), 2.76 (s, 2H), 2.25 (m, 2H), 2.13 (m, 4H), 1.97 (s, 2H), 1.83 (m, 1H), 1.60 (m, 2H), 1.40-1.29 (m, 4H), 0.94 (s, 6H).

Workup

  1. customthe ice bath was removed
  2. stirringThe reaction was stirred 18 hours
  3. concentrationconcentrated
  4. customThe crude product was purified by reverse phase chromatography with ammonium acetate buffer in acetonitrile

Sources & evidence

ORD record
ord-35012292b56345f68d738d15a8a48743
Source dataset
uspto-grants-2016_04
Patent number
US09315488B2

Reaction notes

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