Triethylamine → HCID 66840555, compound

HRID 2206888Notes

Reaction equation

HRID 2206888 reaction equation
[Cl:1][C:2]1[C:3]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:12][CH:11]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[CH2:10]1)=[O:8].[S:27]1[CH:31]=[C:30]([C:32](O)=[O:33])[N:29]=[CH:28]1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(OCC)C>[Cl:1][C:2]1[C:3]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][C:4]=2[S:5][C:6]=1[C:7]([N:9]1[CH2:12][CH:11]([N:13]2[CH2:18][CH2:17][N:16]([C:32]([C:30]3[N:29]=[CH:28][S:27][CH:31]=3)=[O:33])[CH2:15][CH2:14]2)[CH2:10]1)=[O:8]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 3042714-Thiazolecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86680280HCID 86680280, compound

Product 1

HCID 66840555HCID 66840555, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of compound 1d (0.15 mmol), thiazole-4-carboxylic acid 1e (23 mg, 0.18 mmol), and Et3N (0.09 mL, 0.65 mmol) in CH2Cl2 (3 mL) at room temperature was added HATU (68 mg, 0.18 mmol). The reaction mixture was stirred at room temperature for 18 h. It was diluted with diethyl ether, washed with aq. NaHCO3 and aq. NaCl, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2) gave compound 1. 1H NMR (400 MHz, CD3OD): δ 8.80 (d, J=2 Hz, 1H), 8.13 (t, J=0.8 Hz, 1H), 8.03 (d, J=2 Hz, 1H), 8.01 (d, J=8.6 Hz, 1H), 7.73 (dd, J=1.2 Hz, 8.6 Hz, 1H), 4.31 (m, 2H), 4.21 (m, 1H), 4.15 (m, 1H), 4.01 (m, 1H), 3.93 (m, 2H), 3.81 (m, 1H), 3.33 (m, 1H), 2.55-2.40 (m, 4H); MS m/z (M+H+) 515.

Workup

  1. washwashed with aq. NaHCO3 and aq. NaCl
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (silica gel, 3% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-5e5ee23b07084fa78117c0f20c61cc2b
Source dataset
uspto-grants-2016_06
Patent number
US09375430B2

Reaction notes

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