Triethylamine → HCID 72704127, compound

HRID 1049941Notes

Reaction equation

HRID 1049941 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([C:19]([OH:21])=O)[CH:8]=[C:9]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=3)[CH:10]=2)[N:5]=[CH:4][N:3]=1.[NH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:28])[CH3:27].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl.CN(C)C=O>[C:26]([NH:25][CH2:24][CH2:23][NH:22][C:19]([C:7]1[CH:8]=[C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][N:3]=[C:2]2[NH2:1])=[O:21])(=[O:28])[CH3:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66082N-(2-aminoethyl)acetamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86703937HCID 86703937, compound

Product 1

HCID 72704127HCID 72704127, compoundYield 16.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

To a 4 mL screw-cap vial was added 4-amino-6-(3-fluorophenyl)quinazoline-8-carboxylic acid (0.10 mmol, 28 mg) followed by N-(2-aminoethyl)acetamide (2 equiv., 0.20 mmol, 20 mg), HATU (1.1 equiv., 0.11 mmol, 43 mg), dimethylformamide (0.5 mL), and triethylamine (3 equiv., 0.30 mmol, 0.042 mL). The reaction was capped and shaken at 50° C. for 4 h. The reaction was cooled to room temperature, diluted with 2.5 ml dichloromethane and washed with 1 ml water. Organic was concentrated, then the crude was purified by reverse phase HPLC, yielding 6 mg of desired product. 1H NMR (400 MHz, DMSO) δ 11.17-11.07 (t, J=5.6 Hz, 1H), 8.89-8.75 (m, 2H), 8.54-8.50 (s, 1H), 8.44-8.06 (m, 2H), 8.06-7.99 (t, J=5.5 Hz, 1H), 7.75-7.64 (m, 2H), 7.64-7.53 (m, 1H), 7.35-7.22 (m, 1H), 3.53-3.44 (m, 2H), 3.32-3.26 (m, 2H), 1.85-1.82 (s, 3H). LCMS M/Z (M+H)=368.

Workup

  1. customTo a 4 mL screw-cap vial
  2. customThe reaction was capped
  3. temperatureThe reaction was cooled to room temperature
  4. washwashed with 1 ml water
  5. concentrationOrganic was concentrated
  6. customthe crude was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-9ff866d3c78d41d791f457aeb0410bb6
Source dataset
uspto-grants-2016_07
Patent number
US09382241B2

Reaction notes

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