Trifluoroacetic acid → HCID 67225245, compound

HRID 1518862Notes

Reaction equation

HRID 1518862 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-ecc7ea608aac4b40bc8a71e9662a67ab
Source dataset
uspto-grants-2015_07
Patent number
US09072748B2

Reaction notes

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