Dimethylformamide → HCID 178509601, compound

HRID 1179143Notes

Reaction equation

HRID 1179143 reaction equation
[Cl:1][C:2]1[CH:19]=[C:18]([CH2:20][C:21](=O)[C:22]2[CH:26]=[C:25]([C:27](=[O:32])C(Cl)(Cl)Cl)[NH:24][CH:23]=2)[CH:17]=[CH:16][C:3]=1[CH2:4][N:5]1C(=O)C2C(=CC=CC=2)C1=O.[Cl:34][C:35]1[CH:36]=[C:37](NCCO)[CH:38]=[CH:39][C:40]=1[F:41].[C:46]([CH:50]([N:54](C)C)N(C)C)(C)(C)C.[OH2:57].[NH2:58]N.C[N:61]([CH:63]=O)C>C1COCC1.C(O)C>[Cl:34][C:35]1[CH:36]=[C:37]([CH:50]([NH:54][C:27]([C:25]2[NH:24][CH:23]=[C:22]([C:21]3[C:20]([C:18]4[CH:17]=[CH:16][C:3]([CH2:4][NH2:5])=[C:2]([Cl:1])[CH:19]=4)=[CH:63][NH:61][N:58]=3)[CH:26]=2)=[O:32])[CH2:46][OH:57])[CH:38]=[CH:39][C:40]=1[F:41]

Participants

8

Reactant 5

HCID 6228DimethylformamideHCID 24654Hydrazine hydrate (1:1)HCID 129886122-(2-Chloro-4-{2-oxo-2-[5-(2,2,2-trichloro-acetyl)-1H-pyrrol-3-yl-]-ethyl}-benzyl)-isoindole-1,3-dioneHCID 15731881Tert-butyl bis(dimethylamino)-methaneHCID 22349678N-2-hydroxyethyl-3-chloro-4-fluoroaniline

Product 1

HCID 178509601HCID 178509601, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 10 (1.0 mmol) in DMF (5 mL) was added (S) 3-chloro-4-fluoro phenyl glycinol (1.2 mmol), and the solution was stirred for 15 h. The solvent was concentrated under vacuum. To the residue (1.0 mmol) in THF (1 mL) was added tert-butyl bis(dimethylamino)-methane (1 mL, 5 mmol). The mixture was stirred for 15 h at 50° C. and then concentrated under vacuum. To the residue (1 mmol) was added C2H5OH (5 mL) and hydrazine hydrate (1 mL, 20 mmol). The mixture was refluxed for 3 h and cooled to room temperature. The solvents were removed under vacuum and the crude products were purified from preparatory HPLC. This afforded the product 11 as a white solid. 1HNMR (CD3OD) 7.6 (s, 1H), 7.4 (s, 1H), 7.2–7.4 (m, 3H), 7.1–7.2 (m, 1H), 7.0 (t, 1H), 6.8 (d, 2H), 4.9 (t, 1H), 4.1 (s, 2H), 3.6 (dd, 2H).

Workup

  1. concentrationThe solvent was concentrated under vacuum
  2. stirringThe mixture was stirred for 15 h at 50° C.
  3. concentrationconcentrated under vacuum
  4. temperatureThe mixture was refluxed for 3 h
  5. customThe solvents were removed under vacuum
  6. customthe crude products were purified from preparatory HPLC

Sources & evidence

ORD record
ord-de98130f992c46698460f6cf3ab7b2df
Source dataset
uspto-grants-2007_10
Patent number
US07279476B2

Reaction notes

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