3-Methylbenzoic acid → HCID 70032842, compound

HRID 411257Notes

Reaction equation

HRID 411257 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:23][C:24](=[N:54]O)[C:25]1[CH:52]=[CH:51][C:28]([O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:38][CH2:37][N:36]([C:39](=[O:50])[C@H:40]([NH:42][C:43]([C:45]3[S:46][CH:47]=[CH:48][CH:49]=3)=[O:44])[CH3:41])[CH2:35][CH2:34]2)=[CH:27][C:26]=1[F:53]>CN(C=O)C>[F:53][C:26]1[CH:27]=[C:28]([CH:51]=[CH:52][C:25]=1[C:24]1[N:54]=[C:5]([C:4]2[CH:8]=[CH:9][CH:10]=[C:2]([CH3:1])[CH:3]=2)[O:7][N:23]=1)[O:29][CH2:30][CH2:31][CH2:32][N:33]1[CH2:34][CH2:35][N:36]([C:39](=[O:50])[C@H:40]([NH:42][C:43]([C:45]2[S:46][CH:47]=[CH:48][CH:49]=2)=[O:44])[CH3:41])[CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 74183-Methylbenzoic acidHCID 682631,1'-Carbonyldiimidazole2×HCID 131723872HCID 131723872, compound

Product 1

HCID 70032842HCID 70032842, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

3-Methylbenzoic acid (0.3 mmol) was treated with a 0.4 M solution of 1,1′-carbonyldiimidazole (CDI) (0.75 mL, 0.3 mmol) in DMF in a 4 mL vial. After mixing for 30 minutes, a 0.22 M solution of Example 187C (0.75 mL, 0.16 mol) in DMF was added to the vial. The mixture was stirred for 4 hours at room temperature and a 0.4 M solution of CDI (0.5 mL, 0.2 mmol)in DMF was added to the vial. After heating the mixture at 115° C. for 7 hours, the mixture was allowed to cool to room temperature and then was concentrated under reduced pressure. The residue was purified by preparative HPLC to provide the desired product. 1H NMR (CDCl3) δ1.50 (d, 3H), 2.35 (m, 2H), 2.45 (s, 3H), 3.05-3.60 (m, 6H), 3.80-4.25 (m, 6H), 5.05 (m, 1H), 6.80 (m, 2H), 7.00 (m, 1H), 7.08 (m, 1H), 7.40 (m, 2H), 7.50 (m, 1H), 7.60 (m, 1H), 8.00 (m, 2H), 8.05 (m, 1H); MS (APCI+) m/z 564 (M+H)+.

Workup

  1. additionAfter mixing for 30 minutes
  2. temperatureAfter heating the mixture at 115° C. for 7 hours
  3. temperatureto cool to room temperature
  4. concentrationwas concentrated under reduced pressure
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-9a43095315b04882a05f9b37e7a8c888
Source dataset
uspto-grants-2003_05
Patent number
US06559140B2

Reaction notes

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