Isopropylamine → HCID 24803615, compound

HRID 2094230Notes

Reaction equation

HRID 2094230 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[C:13]([C:19]([NH:21][NH2:22])=O)=[N:14][CH:15]=[C:16]([Cl:18])[CH:17]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:23]([F:26])([F:25])[F:24].[N:27]#[C:28]Br.[CH:30]([NH2:33])([CH3:32])[CH3:31]>CC(O)=O>[NH2:27][C:28]1[N:33]([CH:30]([CH3:32])[CH3:31])[C:19]([C:13]2[C:12]([NH:11][S:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:23]([F:26])([F:25])[F:24])[CH:4]=3)(=[O:10])=[O:9])=[CH:17][C:16]([Cl:18])=[CH:15][N:14]=2)=[N:21][N:22]=1

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 10476Cyanogen BromideHCID 59216810HCID 59216810, compound

Product 1

HCID 24803615HCID 24803615, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 35 mL scintillation vial was charged with 4-chloro-N-(5-chloro-2-(hydrazinecarbonyl)pyridine-3-yl)-3-(trifluoromethyl)benzenesulfonamide (500 mg, 1.1 mmol), cyanogenbromide (200 mg, 2.0 mmol) anhydrous MeCN (5 mL). The resultant mixture was heated to 65° C. and stirred for 2 h. After cooling to room temperature, isopropylamine (500 mg, 8.2 mmol) was added followed by AcOH (0.5 mL) and the mixture was heated to 135° C. and stirred for 2 h. After cooling to room temperature, reaction mixture was concentrated under reduced pressure. The residue was further purified through automated normal-phase chromatography (10% to 100% gradient of EtOAc-Hexane) and followed by preparative HPLC (10% to 90% gradient of MeCN-water) and dried (Lyophilizer) to afford the title compound. 1H NMR (400 MHz, CDCl3) 8.28 (d, 1H), 8.18 (d, 1H), 8.10 (d, 1H), 7.90 (dd, 1H), 7.58 (d. 1H), 4.32 (br, 1H), 3.88 (m, 1H), 1.34 (d (d, 6H). MS (ES) [M+H]+ expected 495.0. found 495.0.

Workup

  1. temperaturethe mixture was heated to 135° C.
  2. stirringstirred for 2 h
  3. temperatureAfter cooling to room temperature
  4. customreaction mixture
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was further purified
  7. customdried (Lyophilizer)

Sources & evidence

ORD record
ord-e1b34f500f494935a3026ddfee362f9f
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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