Triethylamine → HCID 86682581, compound

HRID 2036209Notes

Reaction equation

HRID 2036209 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@H:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([OH:32])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:33]#[C:34][NH2:35].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[Cl:27][C:25]1[CH:24]=[CH:23][C:22]([O:28][CH2:29][C:30]([NH:35][C:34]#[N:33])=[O:32])=[C:21]([C@@H:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[CH:26]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 9864CyanamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66654114HCID 66654114, compound

Product 1

HCID 86682581HCID 86682581, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-1-(2-carboxymethoxy-5-chloro-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (138 mg, 0.30 mmol, 1.0 eq.), cyanamide (16 mg, 0.36 mmol, 1.2 eq.), and NEt3 (84 μL, 0.60 mmol, 2 eq.) in DMF (3.3 mL), HATU (137 mg, 0.36 mmol, 1.2 eq.) was added. The reaction mixture was stirred at r.t. for 1 hour. The mixture was purified by prep. HPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, basic conditions) and evaporated to give a pale yellow oil, contaminated with NEt3. The contaminated product was redissolved in AcOEt and washed with 1M aq. HCl soln. and sat. aq. NaCl soln. The org. phase was dried over MgSO4, filtered and concentrated in vacuo to give the desired product as a pale yellow oil.

Workup

  1. customThe mixture was purified by prep
  2. customHPLC (column: Waters XBridge, 30×75 mm, 10 um, UV/MS, basic conditions) and evaporated
  3. customto give a pale yellow oil
  4. washwashed with 1M aq. HCl soln
  5. dry with materialphase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d8e11587fa64453e8223979c34eaffb3
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

Loading…