1,2-Dichloroethane → HCID 136352265, compound

HRID 1047565Notes

Reaction equation

HRID 1047565 reaction equation
[CH:1]1([C:4]([OH:6])=O)[CH2:3][CH2:2]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[NH:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[N:28]=[C:27]1[C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([NH2:44])[CH:42]=2)[N:37]([CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[N:36]=1>CN(C=O)C>[NH:28]1[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[N:26]=[C:27]1[C:35]1[C:43]2[C:38](=[CH:39][CH:40]=[C:41]([NH:44][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:6])[CH:42]=2)[N:37]([CH:45]2[CH2:50][CH2:49][CH2:48][CH2:47][O:46]2)[N:36]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 1363522453-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine

Product 1

HCID 136352265HCID 136352265, compoundYield 66.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cyclopropanecarboxylic acid (6.46 mg, 0.075 mmol), HOBT (15.20 mg, 0.112 mmol), EDC (21.56 mg, 0.112 mmol) and sodium bicarbonate (6.30 mg, 0.075 mmol) was added to a solution of 3-(1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (25 mg, 0.075 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 24 h, and then the solvent was removed in vacuo. Purification by flash column chromatography (6% CH3OH/CH2Cl2) afforded the title compound (20 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.50 (d, 1H, J=1.6 Hz), 7.96 (s, 1H), 7.75 (dd, 1H, J=2.0 and 8.8 Hz), 7.65 (m, 2H), 7.26 (m, 2H), 5.86 (dd, 1H, J=2.0 and 9.2 Hz), 3.97 (m, 1H), 3.81 (m, 1H), 2.63 (m, 1H), 2.14 (m, 2H), 1.82 (m, 2H), 1.68 (m, 2H), 0.99 (m, 2H), 0.87 (m, 2H); ESI-MS [M+H]+: 402.22.

Workup

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

Sources & evidence

ORD record
ord-480219802c4f4c1ea60ec2391b2cee6b
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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