1,2-Dichloroethane → HCID 59375039, compound

HRID 661923Notes

Reaction equation

HRID 661923 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)[C:21]=2[CH3:36])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17](O)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].C1C=[N:41]C2N(O)N=NC=2C=1.[OH-].[NH4+].C(Cl)CCl>C1COCC1>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C:27]([NH:26][C:22]2[C:21]([CH3:36])=[C:20]([C:7]3[C:8]4[C:9]5[C:14](=[CH:13][C:12]([C:17]([NH2:41])=[O:18])=[CH:11][CH:10]=5)[NH:15][C:16]=4[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=3)[CH:25]=[CH:24][CH:23]=2)=[O:35])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 181649HOAtHCID 59375149HCID 59375149, compound

Product 1

HCID 59375039HCID 59375039, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 8-carbamoyl-5-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-2-carboxylic acid (Example 23-1, 30 mg, 0.062 mmol) and HOAT (12.72 mg, 0.093 mmol) in THF (0.4 mL) was treated with 28% aqueous ammonium hydroxide (0.052 mL, 0.374 mmol) and EDC (23.89 mg, 0.125 mmol) and the mixture was stirred at rt. After 22.5 h, the mixture was concentrated and purified by preparative HPLC. The appropriate effluent fractions were concentrated and the residue was treated with NaHCO3 (aq) and extracted three times with EtOAc. The combined organic phases were dried and concentrated to provide 4-(3-(4-fluorobenzamido)-2-methylphenyl)-9H-carbazole-1,7-dicarboxamide as an off-white solid (9.6 mg, 29%). 1H NMR (400 MHz, methanol-d4) δ 8.11 (d, J=1.3 Hz, 1H) 8.03-8.08 (m, 2H) 8.01 (d, J=7.9 Hz, 1H) 7.51-7.55 (m, 1H) 7.41-7.48 (m, 2H) 7.29 (dd, J=7.5, 1.3 Hz, 1H) 7.24 (t, J=8.8 Hz, 2H) 7.08-7.12 (m, 2H) 1.98 (s, 3H). Mass spectrum m/z 481.1 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by preparative HPLC
  3. concentrationThe appropriate effluent fractions were concentrated
  4. additionthe residue was treated with NaHCO3 (aq)
  5. extractionextracted three times with EtOAc
  6. customThe combined organic phases were dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-040baaabf22041d6933adfce6188480e
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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