Methylamine → HCID 58748218, compound

HRID 1162709Notes

Reaction equation

HRID 1162709 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][C:21](=O)[C@H:20]([CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])[CH2:19]1)=[O:17].C1COCC1.[CH3:39][NH2:40].[OH-].[Na+]>O.CC(O)=O>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([N:18]1[CH2:22][CH:21]([NH:40][CH3:39])[C@H:20]([CH2:24][NH:25][C:26]([C:28]2[S:29][C:30]([Cl:33])=[CH:31][CH:32]=2)=[O:27])[CH2:19]1)=[O:17]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58748171HCID 58748171, compound

Product 1

HCID 58748218HCID 58748218, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
22 °C

Procedure

A solution of the (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-oxo-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide (120 mg, example 81.3) and 12 ml of THF saturated with methylamine was treated at 5° C. with 3.5 ml of AcOH until pH=6 and the mixture was warmed to 22° C. After 1.5 h, the mixture was treated with 24 mg of Na(CN)BH3 and stirring was continued for 2.5 h. The mixture was diluted with 5 ml of water, the pH was adjusted to 14 using 3 N NaOH and the solution was extracted with THF. The organic layer was dried and evaporated to give (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-methylamino-pyrrolidine-1-carboxylic acid[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenyl]-amide. Colorless foam. MS 504.0 ([M+H]+)

Workup

  1. waitwas continued for 2.5 h
  2. extractionthe solution was extracted with THF
  3. customThe organic layer was dried
  4. customevaporated

Sources & evidence

ORD record
ord-65cd036bda294def832ddec184cddaaa
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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