Chlorosuccinimide → HCID 53339039, compound

HRID 2405108Notes

Reaction equation

HRID 2405108 reaction equation
[CH:1]1([N:4]2[C:12]3[CH:11]=[C:10]([NH:13][C:14](=[O:26])[C:15]4[CH:20]=[CH:19][C:18]([C@:21]([OH:25])([CH3:24])[CH2:22][OH:23])=[CH:17][CH:16]=4)[N:9]=[CH:8][C:7]=3[CH:6]=[CH:5]2)[CH2:3][CH2:2]1.[Cl:27]N1C(=O)CCC1=O>CN(C)C=O>[Cl:27][C:6]1[C:7]2[CH:8]=[N:9][C:10]([NH:13][C:14](=[O:26])[C:15]3[CH:20]=[CH:19][C:18]([C@:21]([OH:25])([CH3:24])[CH2:22][OH:23])=[CH:17][CH:16]=3)=[CH:11][C:12]=2[N:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 53354694HCID 53354694, compound

Product 1

HCID 53339039HCID 53339039, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

In a 100 mL round bottom flask was added (R)—N-(1-cyclopropyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(1,2-dihydroxypropan-2-yl)benzamide (200 mg, 0.57 mmol) in N,N-dimethylformamide (2.8 mL) to give a light yellow solution. This was followed by addition of N-chlorosuccinimide (76 mg, 0.57 mmol) at room temperature and the mixture was heated to 60° C. After 4 h, another 0.1 eq of N-chlorosuccinimide was added and the mixture was heated for another hour. The mixture was directly loaded onto a silica gel column, eluting with 20-70% EtOAc in hexanes for purification. Product-containing fractions were combined and a pinkish solid was formed upon evaporation of solvents. The solid was collected and washed with 5 ml EtOAc to give the title compound (23, 71 mg, 32%) as a light pink product. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.99-1.06 (m, 2H) 1.10 (dd, J=7.07, 4.55 Hz, 2H) 1.43 (s, 3H) 3.42-3.54 (m, 3H) 4.72 (br. s., 1H) 5.00 (s, 1H) 7.56-7.62 (m, 3H) 8.02 (d, J=8.59 Hz, 2H) 8.52 (d, J=0.76 Hz, 1H) 8.56-8.60 (m, 1H) 10.64 (s, 1H); ESI-MS: m/z 386 (M+H)+.

Workup

  1. customto give a light yellow solution
  2. temperaturethe mixture was heated for another hour
  3. washeluting with 20-70% EtOAc in hexanes for purification
  4. customa pinkish solid was formed upon evaporation of solvents
  5. customThe solid was collected
  6. washwashed with 5 ml EtOAc

Sources & evidence

ORD record
ord-a66eda25754b4c43908a8b95dee49540
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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