1,2-Dichloroethane → HCID 178521727, compound

HRID 1047561Notes

Reaction equation

HRID 1047561 reaction equation
[F:1][C:2]1([F:8])[CH2:4][CH:3]1[C:5](O)=[O:6].N1(O)C2C=CC=CC=2N=N1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[O:28]1[CH2:33][CH2:32][N:31]([C:34]2[CH:58]=[CH:57][C:37]3[NH:38][C:39]([C:41]4[C:49]5[C:44](=[CH:45][CH:46]=[C:47]([NH2:50])[CH:48]=5)[N:43]([CH:51]5[CH2:56][CH2:55][CH2:54][CH2:53][O:52]5)[N:42]=4)=[N:40][C:36]=3[CH:35]=2)[CH2:30][CH2:29]1>CN(C=O)C>[F:1][C:2]1([F:8])[CH2:4][CH:3]1[C:5]([NH:50][C:47]1[CH:48]=[C:49]2[C:44](=[CH:45][CH:46]=1)[N:43]([CH:51]1[CH2:56][CH2:55][CH2:54][CH2:53][O:52]1)[N:42]=[C:41]2[C:39]1[NH:38][C:37]2[CH:57]=[CH:58][C:34]([N:31]3[CH2:32][CH2:33][O:28][CH2:29][CH2:30]3)=[CH:35][C:36]=2[N:40]=1)=[O:6]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27828232,2-Difluorocyclopropane-1-carboxylic acidHCID 178507237HCID 178507237, compound

Product 1

HCID 178521727HCID 178521727, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,2-Difluorocyclopropanecarboxylic acid (6.42 mg, 0.053 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (9.69 mg, 0.072 mmol), EDC (13.74 mg, 0.072 mmol) and sodium bicarbonate (4.01 mg, 0.048 mmol) was added to a solution of 3-(5-morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (20 mg, 0.048 mmol) in DMF (6 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Upon purification by flash chromatography (6% CH3OH/CH2Cl2) afforded the title compound (15 mg). 1H NMR: (400 MHz, CD3OD): δ 8.51 (s, 1H), 7.76-7.72 (m, 1H), 7.68 (m, 1H), 7.58 (m, 1H), 7.05 (m, 2H), 5.86 (dd, 1H, J=2.4 and 9.6 Hz), 3.99 (m, 1H), 3.86 (m, 4H), 3.81 (m, 1H), 3.16 (m, 4H), 2.77-2.69 (m, 1H), 2.61 (m, 1H), 2.18-2.08 (m, 3H), 1.89-1.80 (m, 2H), 1.74-1.68 (m, 2H); ESI-MS [M+H]+: 523.2.

Workup

  1. customthe solvent was removed in vacuo
  2. customUpon purification by flash chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-b84fdbebd66e45c594accb76d84e42e5
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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