Dichloromethane → HCID 67045536, compound

HRID 2203979Notes

Reaction equation

HRID 2203979 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:27])[C:12]=2[N:14]2[CH2:18][CH2:17][C@H:16]([NH:19]C(=O)OC(C)(C)C)[CH2:15]2)[NH:7][CH:6]=1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)[Cl:36]>>[ClH:36].[NH2:19][C@H:16]1[CH2:17][CH2:18][N:14]([C:12]2[C:11]([Br:27])=[CH:10][N:9]=[C:8]3[NH:7][CH:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[C:13]=23)[CH2:15]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67045622HCID 67045622, compound

Product 1

HCID 67045536HCID 67045536, compoundYield 90%

Procedure

(S)-tert-Butyl 1-(3-acetamido-5-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrrolidin-3-ylcarbamate (0.250 g, 0.570 mmol) was placed in DCM (3 mL) at room temperature. TFA (1 mL) was then added, and the reaction was stirred at room temperature for 1 hour and concentrated to dryness. The resulting residue was then purified by reverse phase chromatography (Biotage SP4, C-18 25M+, 0-50% water:ACN). The resulting product was next dissolved in minimal DCM (with MeOH to aid solubility) and added to a stirring solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to give (S)—N-(4-(3-aminopyrrolidin-1-yl)-5-bromo-1H-pyrrolo[2,3-b]pyridin-3-yl)acetamide hydrochloride (0.21 g, 90% yield) as a solid. 1H NMR (400 MHz, D2O) δ 8.17 (s, 1H), 7.24 (s, 1H), 4.10-4.05 (m, 1H), 3.95-3.84 (m, 2H), 3.79-3.70 (m, 2H), 2.37-2.32 (m, 1H), 2.07 (s, 3H), 2.02-1.96 (m, 2H). LCMS (APCI+) m/z 338, 340 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. customThe resulting residue was then purified by reverse phase chromatography (Biotage SP4
  3. dissolutionThe resulting product was next dissolved in minimal DCM (with MeOH to aid solubility)
  4. additionadded to a stirring solution of 1M HCl in ether
  5. filtrationThe resulting solid was filtered
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-f16df4413fc64c869111e0b0921162a9
Source dataset
uspto-grants-2016_06
Patent number
US09365568B2

Reaction notes

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