Methanol → HCID 10223864, compound

HRID 1247589Notes

Reaction equation

HRID 1247589 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH:22]=O)[CH:17]=[N:16][C:15]=3[Cl:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[NH2:26][CH2:27][CH2:28]CO.C([BH3-])#N.[Na+].[CH3:35][OH:36]>C(O)(=O)C>[C:1]12([CH2:11][NH:12][C:13](=[O:25])[C:14]3[CH:19]=[C:18]([CH2:20][CH2:21][CH2:22][NH:26][CH2:27][CH2:28][CH2:35][OH:36])[CH:17]=[N:16][C:15]=3[Cl:24])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 887MethanolHCID 90863-Amino-1-propanolHCID 5003444Sodium cyanoborohydrideHCID 21906677HCID 21906677, compound

Product 1

HCID 10223864HCID 10223864, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of N-(1-adamantylmethyl)-2-chloro-5-(3-oxopropyl)nicotinamide (Example 3(ii)) (0.10 g) in methanol (3 ml) and acetic acid (0.1 ml) was added. 3-aminopropanol (0.042 g) and the resulting solution was stirred for 2 hours and then sodium cyanoborohydride (0.020 g) was added and the reaction mixture stirred for 20 hours. The mixture was concentrated and the residue partitioned between 2M aqueous hydrochloric acid solution and ethyl acetate (2×10 ml). The layers were separated and the organic phase re-extracted with 2M aqueous hydrochloric acid solution (2×10 ml). The combined aqueous extracts were basified with 5M aqueous ammonium hydroxide solution, extracted into ethyl acetate (2×25 ml) and the combined extracts were dried over anhydrous magnesium sulfate, filtered and concentrated to afford the titled compound (0.075 g) as a white solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between 2M aqueous hydrochloric acid solution and ethyl acetate (2×10 ml)
  3. customThe layers were separated
  4. extractionthe organic phase re-extracted with 2M aqueous hydrochloric acid solution (2×10 ml)
  5. extractionextracted into ethyl acetate (2×25 ml)
  6. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-951936ff34ed4d7b93eb8df69f8da959
Source dataset
uspto-grants-2006_10
Patent number
US07129246B2

Reaction notes

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