Isopropylamine → HCID 16222922, compound

HRID 1808973Notes

Reaction equation

HRID 1808973 reaction equation
[F:1][C:2]1[C:3]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[C:4]([C:9]([N:11]2[CH2:14][C:13]([CH2:16][CH:17]=O)([OH:15])[CH2:12]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8].[CH:28]([NH2:31])([CH3:30])[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[F:1][C:2]1[C:3]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([I:26])=[CH:22][C:21]=2[F:27])=[C:4]([C:9]([N:11]2[CH2:12][C:13]([CH2:16][CH2:17][NH:31][CH:28]([CH3:30])[CH3:29])([OH:15])[CH2:14]2)=[O:10])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86621262HCID 86621262, compound

Product 1

HCID 16222922HCID 16222922, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of [1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-hydroxyazetidin-3-yl]acetaldehyde (38.0 mg, 0.078 mmol) in 1,2-dichloroethane (1 mL) was added isopropylamine (27 μL, 0.31 mmol) followed by sodium triacetoxyborohydride (26 mg, 0.12 mmol). The mixture was stirred for 3 h before quenching with 1 drop of concentrated HCl. The quenched mixture was concentrated to dryness, and then purified by preparative HPLC to provide 1-({3,4-difluoro-2-[(2-fluoro-4-iodophenyl)amino]phenyl}carbonyl)-3-{2-[(1-methylethyl)amino]ethyl}azetidin-3-ol (21.5 mg) as a pale yellow solid. 1H NMR (400 MHz, d6-DMSO): δ 8.54 (s, 1H), 7.57 (dd, 1H), 7.38 (dd, 1H), 7.31 (m, 1H), 7.17 (m, 1H), 6.67 (m, 1H), 4.02 (m, 1H), 3.89 (m, 2H), 3.71 (m, 1H), 2.70 (m, 1H), 2.63 (m, 2H), 1.86 (s, 3H), 1.75 (m, 2H), 0.97 (d, 6H); MS (EI) for C21H23F3IN3O2: 534 (MH+).

Workup

  1. custombefore quenching with 1 drop of concentrated HCl
  2. concentrationThe quenched mixture was concentrated to dryness
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-11983991ee29417da4e5753bfc0cc1af
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

Loading…