Isopropanol → HCID 16666335, compound

HRID 2366451Notes

Reaction equation

HRID 2366451 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=O)=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1N=CN(C(N2C=NC=C2)=O)C=1.Cl.Cl.[NH2:36][C:37]1[C:45]([NH2:46])=[CH:44][CH:43]=[CH:42][C:38]=1[C:39]([NH2:41])=[O:40].C(O)(C)C>CN(C)C=O.N1C=CC=CC=1>[C:39]([C:38]1[C:37]2[N:36]=[C:17]([C:16]3[CH:15]=[CH:14][C:13]([CH:9]4[CH2:10][CH2:11][CH2:12][N:8]4[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[CH:21][CH:20]=3)[NH:46][C:45]=2[CH:44]=[CH:43][CH:42]=1)(=[O:40])[NH2:41]

Participants

7

Reactant 4

HCID 3776Isopropanol2×HCID 682631,1'-CarbonyldiimidazoleHCID 450739854-[1-(tert-Butoxycarbonyl)pyrrolidin-2-yl]benzoic acidHCID 534228072,3-Diaminobenzamide dihydrochloride

Product 1

HCID 16666335HCID 16666335, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent

Procedure

N-Boc-4-pyrrolidin-2-ylbenzoic acid (0.29 g) in dimethylformamide (DMF, 1 mL) and pyridine (1 mL) at 40° C. was stirred for 10 minutes, treated with CDI (0.17 g) stirred for 30 minutes, treated with 2,3-diaminobenzamide dihydrochloride (0.22 g), stirred at ambient temperature for 3.5 hours, treated with isopropanol (2 mL), stirred at ambient temperature for 16 hours, treated with isopropanol (5 mL) and hexanes (40 mL) and decanted. The residue was stirred in water (3 mL) at ambient temperature with 2 drops 50% NaOH for 5 hours and filtered. The filtrant was stirred in acetic acid (3 mL) at reflux for 7.5 hours, cooled and concentrated. The concentrate was stirred in dichloromethane (5 mL) and hexane (15 mL) and filtered. 1H NMR (DMSO-d6) δ 13.35 (br, 1H), 9.35 (br, 1H), 8.18 (br d, J=7.8 Hz, 2H), 7.87 (d, J=7.4 Hz, 1H), 7.75 (br, 1H), 7.72 (d, J=8.2 Hz, 1H), 7.40 (br d, J=8.5 Hz, 2H), 7.34 (t, J=7.8 Hz, 1H), 4.79 (brm, 1H), 3.55 (m, 2H), 2.36 (m, 1H), 1.80 (m, 3H), 1.41 (s, 4H), 1.12 (s, 5H).

Workup

  1. stirringstirred at ambient temperature for 3.5 hours
  2. stirringstirred at ambient temperature for 16 hours
  3. customdecanted
  4. stirringThe residue was stirred in water (3 mL) at ambient temperature with 2 drops 50% NaOH for 5 hours
  5. filtrationfiltered
  6. stirringThe filtrant was stirred in acetic acid (3 mL)
  7. temperatureat reflux for 7.5 hours
  8. temperaturecooled
  9. concentrationconcentrated
  10. stirringThe concentrate was stirred in dichloromethane (5 mL)
  11. filtrationhexane (15 mL) and filtered

Sources & evidence

ORD record
ord-e1e43b7ed37344e58a7dd9bc1618e024
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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