Hydrochloric Acid → HCID 57542280, compound

HRID 2080286Notes

Reaction equation

HRID 2080286 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:36]=[CH:35][C:12]([C:13]([NH:15][CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][N:18]2[C:22](=[O:34])[CH2:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)=[O:14])=[C:11]([NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=2)[N:10]=1)#[N:2].Cl>CO>[NH2:26][CH2:25][CH2:24][CH2:23][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][CH:17]1[CH2:16][NH:15][C:13](=[O:14])[C:12]1[CH:35]=[CH:36][C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[C:1]#[N:2])=[N:10][C:11]=1[NH:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[CH:41]=1)=[O:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57542726Tert-butyl 4-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate

Product 1

HCID 57542280HCID 57542280, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 4-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (71 mg, 0.11 mmol) in MeOH (5.0 mL) was added HCl (1.0 mL, 4 mmol, 4 M in dioxane). The reaction mixture was stirred at r.t. for 2 h. LC/MS indicated the reaction was complete. The reaction mixture was concentrated under reduced pressure and the crude was purified on RP-HPLC using a mixture of acetonitrile (0.1% TFA) and water (0.1% TFA) to give N-((1-(4-aminobutanoyl)pyrrolidin-2-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide as a pale yellow solid (57.1 mg, 68%). LRMS (M+H+) m/z 529.2.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude was purified on RP-HPLC
  3. additiona mixture of acetonitrile (0.1% TFA) and water (0.1% TFA)

Sources & evidence

ORD record
ord-cd84e6c9deb74c0898f00459232fd44e
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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