N-bromobutanimide → HCID 53354697, compound

HRID 2405106Notes

Reaction equation

HRID 2405106 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][CH:7]=1)([OH:5])[CH3:4].[Br:26]N1C(=O)CCC1=O>ClCCl>[Br:26][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])=[CH:7][CH:8]=3)=[CH:14][C:15]=2[N:21]([CH2:22][CH3:23])[CH:20]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 53354592HCID 53354592, compound

Product 1

HCID 53354697HCID 53354697, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL pear flask was added (R)-4-(1,2-dihydroxypropan-2-yl)-N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)benzamide (13, 125 mg, 0.368 mmol) in dichloromethane (3.7 ml). At 0° C., 1-bromopyrrolidine-2,5-dione (66 mg, 0.37 mmol) was added to the mixture, and the mixture was kept in the refrigerator over the weekend. After concentration in vacuo, the crude product was purified by preparatory HPLC (TFA mode, 15-65% ACN/water). Combined fractions were neutralized by NaHCO3, concentrated and extracted into EtOAc. Combined organic layers were dried over MgSO4, filtered and concentrated. The residue was then re-suspended in ACN and water, and then freeze dried to give the desired product (R)—N-(3-bromo-1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-4-(1,2-dihydroxypropan-2-yl)benzamide (20, 10 mg, 7%) as a light orange powder. 1H NMR (DMSO-d6) δ 10.62 (s, 1H), 8.50 (s, 1H), 8.36 (s, 1H), 7.97-8.05 (m, 2H), 7.70 (s, 1H), 7.54-7.61 (m, 2H), 5.00 (s, 1H), 4.71 (t, J=5.8 Hz, 1H), 4.21 (d, J=7.1 Hz, 2H), 3.46 (dd, J=5.8, 2.3 Hz, 2H), 1.42 (s, 4H), 1.39 (t, J=7.2 Hz, 3H); ESI-MS: m/z 418 (M+H)+.

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe crude product was purified by preparatory HPLC (TFA mode, 15-65% ACN/water)
  3. concentrationconcentrated
  4. extractionextracted into EtOAc
  5. dry with materialCombined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. dry with materialwater, and then freeze dried

Sources & evidence

ORD record
ord-b2c5b9280aa54ac3864d915a69a97ac5
Source dataset
uspto-grants-2014_08
Patent number
US08802695B2

Reaction notes

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