Hydrochloric Acid → (R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinic acid

HRID 924017Notes

Reaction equation

HRID 924017 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([C:17]3[CH:18]=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:15][C:10]([C:11]([O:13]C)=[O:12])=[CH:9][N:8]=2)[CH2:3]1.[OH-].[Na+].Cl>>[OH:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([C:17]3[CH:18]=[N:19][CH:20]=[N:21][CH:22]=3)=[CH:15][C:10]([C:11]([OH:13])=[O:12])=[CH:9][N:8]=2)[CH2:3]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 118198944(R)-Methyl 6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinate

Product 1

HCID 118195186(R)-6-(3-Hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinic acid

Procedure

(R)-Methyl 6-(3-hydroxypyrrolidin-1-yl)-5-(pyrimidin-5-yl)nicotinate (Stage 170.2, 640 mg, 4.26 mmol) was added to 2 M NaOH (2 mL) and stirred 30 min at RT until complete dissolution. The RM was acidified (pH=2) with 2 M HCl and the solid which precipitated was filtered to afford the title compound as a white crystalline powder. HPLC (Condition 4) tR=2.19 min, UPLC-MS (Condition 7) m/z=287.1 [M+H]+.

Workup

  1. customthe solid which precipitated
  2. filtrationwas filtered

Sources & evidence

ORD record
ord-79d65dfc445c49f1b89eb1853cd9218e
Source dataset
uspto-grants-2016_03
Patent number
US09278981B2

Reaction notes

Loading…