Hydrochloric Acid → HCID 67102519, compound

HRID 2080292Notes

Reaction equation

HRID 2080292 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:35]=[CH:34][C:12]([C:13]([NH:15][CH2:16][C@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[N:18]2[CH2:23][CH2:24][CH2:25][NH:26]C(=O)OC(C)(C)C)=[O:14])=[C:11]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=2)[N:10]=1)#[N:2].[ClH:46]>CO>[ClH:46].[NH2:26][CH2:25][CH2:24][CH2:23][N:18]1[C:19](=[O:22])[CH2:20][CH2:21][C@@H:17]1[CH2:16][NH:15][C:13](=[O:14])[C:12]1[CH:34]=[CH:35][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:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57542509HCID 57542509, compound

Product 1

HCID 67102519HCID 67102519, compoundYield 113.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 3-(2-((6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamido)methyl)-5-oxopyrrolidin-1-yl)propylcarbamate (72 mg, 0.12 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 to give (R)—N-((1-(3-aminopropyl)-5-oxopyrrolidin-2-yl)methyl)-6-(2-cyanophenyl)-2-(3-fluorophenethylamino)nicotinamide hydrogen chloride (75 mg, quantitative). LRMS (M+H+) m/z 515.1.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-27c525bb29cb485bbd27e93baaa97a32
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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