HCID 59347403, compound → HCID 59347400, compound

HRID 539847Notes

Reaction equation

HRID 539847 reaction equation
[P:1]([O:13][CH2:14][N:15]1[C:19]2=[C:20]([N:26]3[CH:30]=[N:29][C:28]([CH3:31])=[N:27]3)[N:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]2[C:17]([C:32](=[O:50])[C:33]([N:35]2[CH2:40][CH2:39][C:38](=[C:41]([C:48]#[N:49])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH2:37][CH2:36]2)=[O:34])=[CH:16]1)([O:8]C(C)(C)C)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]>C(O)(C(F)(F)F)=O.ClCCl>[P:1]([OH:8])([O:13][CH2:14][N:15]1[C:19]2=[C:20]([N:26]3[CH:30]=[N:29][C:28]([CH3:31])=[N:27]3)[N:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]2[C:17]([C:32](=[O:50])[C:33]([N:35]2[CH2:36][CH2:37][C:38](=[C:41]([C:48]#[N:49])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH2:39][CH2:40]2)=[O:34])=[CH:16]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[P:1]([OH:3])([OH:8])([O:13][CH2:14][N:15]1[C:19]2=[C:20]([N:26]3[CH:30]=[N:29][C:28]([CH3:31])=[N:27]3)[N:21]=[CH:22][C:23]([O:24][CH3:25])=[C:18]2[C:17]([C:32](=[O:50])[C:33]([N:35]2[CH2:36][CH2:37][C:38](=[C:41]([C:48]#[N:49])[C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][N:43]=3)[CH2:39][CH2:40]2)=[O:34])=[CH:16]1)=[O:2]

Participants

5

Reactant 1

HCID 59347403HCID 59347403, compound

Product 2

HCID 59347400HCID 59347400, compoundHCID 59347414HCID 59347414, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Di-tert-butyl (3-(2-(4-(cyano(pyridin-2-yl)methylene)piperidin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl phosphate (IIe) was dissolved in 8 ml of a mixed solution of TFA and dichloromethane (10% TFA/CH2Cl2) and the mixture was stirred for three hours. All the solvents were removed under vacuum and the residue was purified using a Shimadzu automated preparative HPLC System to give 25 mg of tert-butyl (3-(2-(4-(cyano(pyridin-2-yl)methylene)piperidin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl hydrogen phosphate (II′e) and 33 mg of (3-(2-(4-(cyano(pyridin-2-yl)methylene)piperidin-1-yl)-2-oxoacetyl)-4-methoxy-7-(3-methyl-1H-1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-1-yl)methyl dihydrogen phosphate (Ie).

Workup

  1. customAll the solvents were removed under vacuum
  2. customthe residue was purified

Sources & evidence

ORD record
ord-995e7d87a1034b9bb389e677134aa752
Source dataset
uspto-grants-2014_10
Patent number
US08871771B2

Reaction notes

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