Ethanolamine → HCID 178523446, compound

HRID 1672491Notes

Reaction equation

HRID 1672491 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:20]([OH:22])=O)[C:5]2[CH:6]=[C:7]([NH:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]3)[N:8]=[CH:9][C:10]=2[CH:11]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH2:54][CH2:55][CH2:56][OH:57]>CC(N(C)C)=O>[F:1][C:2]1[CH:3]=[C:4]([C:20]([NH:54][CH2:55][CH2:56][OH:57])=[O:22])[C:5]2[CH:6]=[C:7]([NH:12][C@H:13]3[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]3)[N:8]=[CH:9][C:10]=2[CH:11]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178524527HCID 178524527, compound

Product 1

HCID 178523446HCID 178523446, compoundYield 19.3%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

7-fluoro-3-[(trans-4-hydroxycyclohexyl)amino]isoquinoline-5-carboxylic acid (23.0 mg, 0.076 mmol) in 5 ml DMA was treated with HATU (62.1 mg, 0.16 mmol) and triethylamine (49.5 mg, 0.49 mmol). After 1 hour, 2-aminoethanol (15.0 mg, 0.25 mmol) was added and the solution was heated to 50° C. for 2 hours. The reaction was monitored by LC/MS to show no start acid left. The solvent was removed under vacuum and the crude was dissolved in CH2Cl2 and washed with 1 M NaHCO3 aqueous. The organic layers were dried over MgSO4. The crude material after removal of the solvent was purified by prepHPLC to give 5.8 mg (yield 19.3%). 1H NMR (400 MHz, MeOD) ppm 1.21-1.56 (m, 4H), 1.87-2.20 (m, 4H), 3.48-3.67 (m, 4H), 3.77 (m, 2H), 7.02 (s, 1H), 7.46-7.69 (m, 2H), 8.78 (s, 1H). HRMS: m/z 348.17226[M+H]+), calc. 348.17180. MS m/z, (APCI); 348.2 ([M+H]+).

Workup

  1. waitleft
  2. customThe solvent was removed under vacuum
  3. dissolutionthe crude was dissolved in CH2Cl2
  4. washwashed with 1 M NaHCO3 aqueous
  5. dry with materialThe organic layers were dried over MgSO4
  6. customThe crude material after removal of the solvent
  7. customwas purified by prepHPLC
  8. customto give 5.8 mg (yield 19.3%)

Sources & evidence

ORD record
ord-8a8ddc97a96e41e881feaeac8d29c77b
Source dataset
uspto-grants-2011_08
Patent number
US07998978B2

Reaction notes

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