Trifluoroacetic acid → (R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

HRID 2275046Notes

Reaction equation

HRID 2275046 reaction equation
C(OC(=O)[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.CO>[NH2:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([C:16]2[CH:38]=[C:37]([O:39][CH3:40])[C:19]3[N:20]([CH3:36])[C:21]([C:23]4[N:31]([CH2:32][CH:33]5[CH2:35][CH2:34]5)[C:26]5=[N:27][CH:28]=[CH:29][CH:30]=[C:25]5[CH:24]=4)=[N:22][C:18]=3[CH:17]=2)=[O:15])[CH2:9]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118178622(R)-tert-Butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate

Product 1

HCID 73052939(R)-(3-Aminopiperidin-1-yl)(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl(1-(2-(1-(cyclopropylmethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-7-methoxy-1-methyl-1H-benzo[d]imidazole-5-carbonyl)piperidin-3-yl)carbamate (1.5587 g, 2.79 mmol) in DCM (10 ml) was added TFA (5 mL, 65.3 mmol) dropwise. The reaction mixture was stirred for 30 minutes and then concentrated under vacuum to afford an oil. The oil was dissolved in methanol and loaded onto a 70 g SCX cartridge. The column was washed with MeOH (2CV) and the product collected as the free base with 2M ammonia in methanol (3CV). The product was concentrated in vacuo yield a crude product. This was purified by high pH MDAP (Method E). Appropriate fractions were combined and concentrated in vacuo to yield the title compound as a white solid, 1.127 g.

Workup

  1. concentrationconcentrated under vacuum
  2. customto afford an oil
  3. washThe column was washed with MeOH (2CV)
  4. customthe product collected as the free base with 2M ammonia in methanol (3CV)
  5. concentrationThe product was concentrated in vacuo
  6. customyield a crude product
  7. customThis was purified by high pH MDAP (Method E)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-37ec4487544742439e83139f93573e9a
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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