Dichloromethane → HCID 67045404, compound

HRID 875824Notes

Reaction equation

HRID 875824 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH:21]3[CH2:23][CH2:22]3)=[CH:19][N:18]=[C:17]3[N:24](C(OC(C)(C)C)=O)[CH:25]=[C:26]([NH:27][C:28](=[O:32])[CH:29]([CH3:31])[CH3:30])[C:16]=23)[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C(Cl)[Cl:48]>>[ClH:48].[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[C:20]([CH:21]3[CH2:22][CH2:23]3)=[CH:19][N:18]=[C:17]3[NH:24][CH:25]=[C:26]([NH:27][C:28](=[O:32])[CH:29]([CH3:30])[CH3:31])[C:16]=23)[CH2:10]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 67045129HCID 67045129, compound

Product 1

HCID 67045404HCID 67045404, compoundYield 74%

Procedure

(R)-tert-Butyl 4-(3-(tert-butoxycarbonylamino)piperidin-1-yl)-5-cyclopropyl-3-isobutyramido-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.150 g, 0.277 mmol) was placed in DCM (5 mL). TFA (1 mL) was then added, and the reaction was stirred at room temperature for 1 hour and concentrated to dryness. The resulting product was dissolved in minimal DCM (with MeOH to aid solubility) and added to a stirred solution of 1M HCl in ether. The resulting solid was filtered, washed with ether and dried to give (R)—N-(4-(3-aminopiperidin-1-yl)-5-cyclopropyl-1H-pyrrolo[2,3-b]pyridin-3-yl)isobutyramide hydrochloride (0.085 g, 74% yield) as a solid. 1H NMR (400 MHz, D2O) δ 7.88 (s, 1H), 7.25 (s, 1H), 3.96-3.93 (m, 1H) 3.53-3.49 (m, 1H) 3.42-3.37 (m, 2H), 3.32-3.27 (m, 1H), 3.22-3.17 (m, 1H), 2.70-3.63 (m, 1H), 2.14-2.12 (m, 1H), 1.89-1.86 (m, 1H), 1.80-1.77 (m, 1H), 1.69-1.66 (m, 1H), 1.54-1.52 (m, 1H), 1.12-1.09 (m, 6H), 0.99-0.96 (m, 2H), 0.66-0.62 (m, 2H); LCMS (APCI+) m/z 342 (M+H)+.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe resulting product was dissolved in minimal DCM (with MeOH to aid solubility)
  3. additionadded to a stirred solution of 1M HCl in ether
  4. filtrationThe resulting solid was filtered
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-1e6479760d574a49986297ab606afc06
Source dataset
uspto-grants-2015_03
Patent number
US08981085B2

Reaction notes

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