3-Amino-1-propanol → HCID 59437560, compound

HRID 2382901Notes

Reaction equation

HRID 2382901 reaction equation
Cl[C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[N:24]=[C:12]3[CH:13]=[CH:14][CH:15]=[C:16]([NH:17][CH:18]4[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]4)[N:11]3[N:10]=2)=[O:7])=[CH:4][N:3]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].C(N(CC)C(C)C)(C)C>C(O)CCC>[CH:18]1([NH:17][C:16]2[N:11]3[N:10]=[C:9]([NH:8][C:6](=[O:7])[C:5]4[CH:25]=[CH:26][C:2]([NH:27][CH2:28][CH2:29][CH2:30][OH:31])=[N:3][CH:4]=4)[N:24]=[C:12]3[CH:13]=[CH:14][CH:15]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 81531DiisopropylethylamineHCID 25212769HCID 25212769, compound

Product 1

HCID 59437560HCID 59437560, compoundYield 30.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a biotage initiator microwave vial (0.2-0.5 mL) containing 6-chloro-N-(5-cyclohexylamino-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-nicotinamide ((B11), 0.27 mmol, 100 mg, 1 eq.), 3-aminopropan-1-ol (0.54 mmol, 0.028 mL, 2 eq.) and N,N-diisopropylethylamine (0.54 mmol, 0.094 mL, 2 eq.) in butanol (2 mL), was capped and heated in a biotage initiator 60 microwave for 30 minutes at 180° C., and a further 10 minutes at 210° C. The solvent was removed in vacuo and the residue dissolved in DMSO (1.5 mL) and purified by reverse phase preparatory HPLC to give the title compound as a white solid (33.4 mg, 30%). HPLC, Rt: 2.37 min (purity: 92%). LC/MS M+(ESI): 410.2, M−(ESI) 408.2.

Workup

  1. customwas capped
  2. customa further 10 minutes
  3. customat 210° C
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in DMSO (1.5 mL)
  6. custompurified by reverse phase preparatory HPLC

Sources & evidence

ORD record
ord-937a5f5c6715411bbdec68da85d221f5
Source dataset
uspto-grants-2012_09
Patent number
US08263595B2

Reaction notes

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