Hydrochloric Acid → HCID 178522488, compound

HRID 1910148Notes

Reaction equation

HRID 1910148 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([NH:17][C:18]([C:20]3[C:28]4[NH:27][C:26]([NH:29][C:30]([C:32]5[N:33]=[CH:34][C:35]6[C:40]([CH:41]=5)=[CH:39][CH:38]=[CH:37][CH:36]=6)=[O:31])=[N:25][C:24]=4[CH:23]=[CH:22][CH:21]=3)=[O:19])[S:16][C:10]=2[CH2:9]1)=O)(C)(C)C.Cl>CO>[N:14]1[C:11]2[CH2:12][CH2:13][NH:8][CH2:9][C:10]=2[S:16][C:15]=1[NH:17][C:18]([C:20]1[C:28]2[NH:27][C:26]([NH:29][C:30]([C:32]3[N:33]=[CH:34][C:35]4[C:40]([CH:41]=3)=[CH:39][CH:38]=[CH:37][CH:36]=4)=[O:31])=[N:25][C:24]=2[CH:23]=[CH:22][CH:21]=1)=[O:19]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1784516582-({2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carbonyl}-amino)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 178522488HCID 178522488, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.2 g (0.35 mmol) of 2-({2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carbonyl}-amino)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester in methanol (1 mL) was added HCl solution (5 mL, 4M HCl in 1,4-dioxane). The mixture was stirred at room temperature for 30 min. The conversion was checked by LCMS. After removal of the organic phase, the residue was diluted with DCM (50 mL) and the organic phase was washed with sat. aq. Na2CO3 solution, water, brine, dried over Na2SO4 and concentrated to afford 160 mg (100%) of isoquinoline-3-carboxylic acid [7-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-amide. LCMS: 470 (M+1)+.

Workup

  1. customAfter removal of the organic phase
  2. additionthe residue was diluted with DCM (50 mL)
  3. washthe organic phase was washed with sat. aq. Na2CO3 solution, water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a9171bf76bfd447da2bc35125c035405
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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