Chlorosuccinimide → HCID 53353298, compound

HRID 2405115Notes

Reaction equation

HRID 2405115 reaction equation
[OH:1][CH2:2][C@@:3]([C:6]1[CH:25]=[CH:24][C:9]([C:10]([NH:12][C:13]2[N:18]=[CH:17][C:16]3[CH:19]=[CH:20][N:21]([CH2:22][CH3:23])[C:15]=3[CH:14]=2)=[O:11])=[CH:8][C:7]=1[CH3:26])([OH:5])[CH3:4].C1C(=O)N([Cl:34])C(=O)C1>CN(C)C=O.CO>[Cl:34][C:19]1[C:16]2[CH:17]=[N:18][C:13]([NH:12][C:10](=[O:11])[C:9]3[CH:24]=[CH:25][C:6]([C@:3]([OH:5])([CH3:4])[CH2:2][OH:1])=[C:7]([CH3:26])[CH:8]=3)=[CH:14][C:15]=2[N:21]([CH2:22][CH3:23])[CH:20]=1

Participants

5

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 53353202HCID 53353202, compound

Product 1

HCID 53353298HCID 53353298, compoundYield 25.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(R)-4-(1,2-dihydroxypropan-2-yl)-N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-3-methylbenzamide (40 mg, 0.11 mmol) was dissolved in N,N-dimethylformamide (0.57 mL) to give a light yellow solution. NCS (14 mg, 0.10 mmol) was then added at room temperature. The mixture was heated mixture at 60° C.; after 3 hr, another 15 mg of NCS was added, and the reaction completed after 1 hr. The mixture was diluted with MeOH (1 ml) and then purified by preparatory HPLC (basic mode, 20-70% ACN in water). Product-containing fractions were combined, concentrated and freeze-dried to obtain the title compound as a tan colored solid (10 mg, 23%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.38 (t, J=7.20 Hz, 3H) 1.48 (s, 3H) 2.58 (s, 3H) 3.58-3.64 (m, 2H) 4.19 (q, J=7.24 Hz, 2H) 4.77 (br. s., 1H) 4.92 (br. s., 1H) 7.55 (d, J=8.34 Hz, 1H) 7.68 (s, 1H) 7.76-7.88 (m, 2H) 8.36 (d, J=0.76 Hz, 1H) 8.59 (d, J=1.01 Hz, 1H) 10.58 (s, 1H); ESI-MS: m/z 388 (M+H)+.

Workup

  1. customto give a light yellow solution
  2. waitthe reaction completed after 1 hr
  3. custompurified by preparatory HPLC (basic mode, 20-70% ACN in water)
  4. concentrationconcentrated
  5. customfreeze-dried

Sources & evidence

ORD record
ord-79db4b5e2ca947bc82e964521e514109
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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