Hydrochloric Acid → HCID 67045181, compound

HRID 408445Notes

Reaction equation

HRID 408445 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[C:15]3[C:10](=[N:11][CH:12]=[C:13]([O:30][CH2:31][CH2:32][O:33][CH3:34])[C:14]=3[N:16]3[CH2:21][CH2:20][CH2:19][C@@H:18]([NH:22]C(=O)OC(C)(C)C)[CH2:17]3)[NH:9][CH:8]=2)=[O:5])[CH2:3][CH2:2]1.[ClH:35]>CC(O)C>[ClH:35].[NH2:22][C@@H:18]1[CH2:19][CH2:20][CH2:21][N:16]([C:14]2[C:13]([O:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:12][N:11]=[C:10]3[NH:9][CH:8]=[C:7]([NH:6][C:4]([CH:1]4[CH2:2][CH2:3]4)=[O:5])[C:15]=23)[CH2:17]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67045415HCID 67045415, compound

Product 1

HCID 67045181HCID 67045181, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(R)-tert-Butyl 1-(3-(cyclopropanecarboxamido)-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-4-yl)piperidin-3-ylcarbamate (0.110 g, 0.232 mmol) was dissolved in 5N HCl (2.32 mL, 11.6 mmol) in IPA and stirred at room temperature for 2 hours. The reaction was concentrated to dryness, suspended in acetonitrile (5 mL) and stirred at room temperature for 30 minutes. The resulting precipitate was filtered and dried to yield (R)—N-(4-(3-aminopiperidin-1-yl)-5-(2-methoxyethoxy)-1H-pyrrolo[2,3-b]pyridin-3-yl)cyclopropanecarboxamide hydrochloride (0.094 g, 90.7% yield) as a solid. 1H NMR (400 MHz, D2O) δ 7.82 (s, 1H), 7.21 (s, 1H), 4.13 (m, 2H), 3.75-3.81 (m, 3H), 3.47 (m, 2H), 3.30 (s, 3H), 3.22 (m, 2H), 2.07 (m, 1H), 1.74 (m, 2H), 1.57-1.65 (m, 2H), 0.88 (m, 2H), 0.93 (m 2H). LCMS (APCI+) m/z 374.2 (M+H).

Workup

  1. concentrationThe reaction was concentrated to dryness
  2. stirringstirred at room temperature for 30 minutes
  3. filtrationThe resulting precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-1afaedeee0bf4c77aa59f232cae43374
Source dataset
uspto-grants-2014_06
Patent number
US08758830B2

Reaction notes

Loading…