Hydrochloride methanol → HCID 67959638, compound

HRID 1529359Notes

Reaction equation

HRID 1529359 reaction equation
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([NH:30]C(=O)CC)[CH:28]=4)[N:23](C(OC(C)(C)C)=O)[CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C.CO.Cl>>[NH2:8][CH:9]1[CH2:10][CH2:11][N:12]([C:15]2[N:20]=[C:19]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([NH2:30])[CH:28]=4)[NH:23][CH:22]=3)[CH:18]=[N:17][CH:16]=2)[CH2:13][CH2:14]1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 67958305HCID 67958305, compound

Product 1

HCID 67959638HCID 67959638, compoundYield 31.2%

Conditions

Temperature
60 °C

Procedure

A mixture of tert-butyl 3-(6-(4-(tert-butoxycarbonylamino)piperidin-1-yl)pyrazin-2-yl)-5-propionamido-1H-indole-1-carboxylate (150 mg, 0.26 mmol) and 3 N MeOH—HCl (3 mL) was stirred at 60° C. overnight. The reaction mixture was quenched with water and neutralized with K2CO3. The resulting precipitate was filtered, washed with water and dried to obtain the crude product. The crude product was purified by prep HPLC (column: Zorbax Eclipse XDBC Prep C18 5 μm 21.2*150 mm; flow rate: 15.0 mL/min; mobile phase: A: 0.1% TFA in water. B: ACN+MeOH (1:1); gradient: % B, 10% to 50%) to obtain the title compound (25 mg, 28%). MS (ESI, pos. ion) m/z: 309.1 (M+1).

Workup

  1. customThe reaction mixture was quenched with water and neutralized with K2CO3
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried
  5. customto obtain the crude product
  6. customThe crude product was purified by prep HPLC (column

Sources & evidence

ORD record
ord-6c1040dfce504b7594dae039b4223b5e
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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