Propiolic Acid → HCID 86713610, compound

HRID 524094Notes

Reaction equation

HRID 524094 reaction equation
[NH2:1][CH2:2][C:3]1[C:4]2[N:5]([C:9]([C:12]3[CH:13]=[C:14]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:30])([F:29])[F:28])=[O:24])[CH:15]=[C:16]([O:18][CH:19]([CH3:21])[CH3:20])[CH:17]=3)=[CH:10][N:11]=2)[CH:6]=[CH:7][CH:8]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:64](O)(=[O:67])[C:65]#[CH:66]>C(Cl)Cl>[CH:19]([O:18][C:16]1[CH:17]=[C:12]([C:9]2[N:5]3[CH:6]=[CH:7][CH:8]=[C:3]([CH2:2][NH:1][C:64](=[O:67])[C:65]#[CH:66])[C:4]3=[N:11][CH:10]=2)[CH:13]=[C:14]([NH:22][C:23]([NH:25][CH2:26][C:27]([F:29])([F:30])[F:28])=[O:24])[CH:15]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 10110Propiolic AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86713609HCID 86713609, compound

Product 1

HCID 86713610HCID 86713610, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(3-(8-(aminomethyl)imidazo[1,2-a]pyridin-3-yl)-5-isopropoxyphenyl)-3-(2,2,2-trifluoroethyl)urea (26 mg, 0.062 mmol) in DCM (3 ml) was added DIEA (0.075 ml, 0.432 mmol) and HATU (35.2 mg, 0.093 mmol) and finally propiolic acid (4.95 μl, 0.080 mmol). Reaction was stirred for 30 minutes at room temperature. Reaction was loaded directly onto silica column and purified by flash chromatography (0-10% CH2Cl2/MeOH) to give the title compound (19 mg, 0.040 mmol, 65.0% yield) as an off white solid. MS (ES+) C23H22F3N5O3 requires: 473. found: 474 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 9.34 (s, 1H), 8.92 (s, 1H), 8.47 (d, J=6.8 Hz, 1H), 7.74 (s, 1H), 7.17 (d, J=1.9 Hz, 2H), 7.10 (s, 1H), 6.98 (s, 1H), 6.82 (s, 1H), 6.74 (s, 1H), 4.69-4.58 (m, 2H), 3.93 (dd, J=9.7, 6.4 Hz, 2H), 2.72-2.64 (m, 1H), 1.30-1.19 (m, 6H).

Workup

  1. customReaction
  2. customReaction
  3. custompurified by flash chromatography (0-10% CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-9f7e60f8d0054fbb89c11b51b4eb6b65
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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