Diisopropylethylamine → HCID 178523100, compound

HRID 874736Notes

Reaction equation

HRID 874736 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=2)[NH:4][N:3]=1.[CH:14]1([CH:17]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[NH2:18])[CH2:16][CH2:15]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[CH:14]1([CH:17]([C:19]2[S:20][CH:21]=[CH:22][N:23]=2)[NH:18][C:11]([C:8]2[CH:9]=[C:10]3[C:5](=[CH:6][CH:7]=2)[NH:4][N:3]=[C:2]3[I:1])=[O:13])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 46785163cyclopropyl(1,3-thiazol-2-yl)methanamineHCID 178524181HCID 178524181, compound

Product 1

HCID 178523100HCID 178523100, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The title compound was synthesized according to General Method A utilizing 3-iodo-1H-indazole-5-carboxylic acid (255 mg, 0.88 mmol), cyclopropyl(thiazol-2-yl)methanamine (150 mg, 0.97 mmol), TBTU (310 mg, 0.97 mmol), DIPEA (0.31 mL, 1.8 mmol), and DMF (8 mL). The reaction was stirred at 0° C. for 1 h. The crude reaction was subsequently diluted with H2O. A filtration and washing (H2O) of the precipitate provided the desired product as a beige solid (195 mg, 52%). The product used without further purification. 1H NMR (400 MHz, CD3OD) δ ppm 8.16 (br. s., 1H), 7.99 (m., 1H), 7.77 (br. s., 1H), 7.46-7.67 (m, 2H), 1.45-1.68 (m, 1H), 0.46-0.90 (m, 4H); MS ESI 425.0 [M+H]+, calcd for [C15H13IN4OS+H]+ 425.0.

Workup

  1. customThe title compound was synthesized
  2. customThe crude reaction
  3. filtrationA filtration
  4. washwashing (H2O) of the precipitate

Sources & evidence

ORD record
ord-bde75df797a34269bbae75374c7924f0
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

Loading…